Capsaicin

Iupac Name：(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

Molecular Weight：305.41200

Modify Date.: 2022-11-29 12:28

Introduction: Capsaicin is the main chemical that makes chili peppers hot. Capsaicin is an animal repellent that is also used against insects and mites. Capsaicin was first registered for use in the United States in 1962. The U.S. Environmental Protection Agency considers it to be a biochemical pesticide because it is a naturally occurring substance. View more+

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1. Names and Identifiers

1.1 Name: Capsaicin
1.2 Synonyms: (1Z,6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenimidic acid (6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide (6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide (E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDE (E)-8-Methyl-N-vanillyl-6-nonenamide (E)-CAPSAICIN (E)-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide (E)-N-([4-HYDROXY-3-METHOXYPHENYL]METHYL)8-METHYL-6-NONEAMIDE (E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide (E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)- 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (6E)- 6-Nonenimidic acid, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (1Z,6E)- 8-methyl N-vanillyl-6-nonenamide 8-Methyl-N-vanillyl-6-nonenamide 8-Methyl-N-vanillyl-6-nonenamide, (E)- 8-Methyl-N-vanillyl-trans-6-nonenamide 8-Methyl-N-vanillyl-trans-6-nonenamide,Capsaicin Axsain Capsaicin (Natural) Capsaicin, (6E)- CAPSAICIN, NATURAL CAPSAICINE Capsidol EINECS 206-969-8 FEMA 3404 MFCD00017259 N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide N-vanillyl-8-methyl-non-6-enamide Qutenza Styptysat trans-8-methyl-n-vanillyl-6-nonenamide Transacin trans-Capsaicin Zostrix

1.3 CAS No.: 404-86-4

1.4 CID: 1548943

1.5 EINECS(EC#): 206-969-8

1.6 Molecular Formula: C18H27NO3 (isomer)

1.7 Inchi: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

1.8 InChkey: YKPUWZUDDOIDPM-SOFGYWHQSA-N

1.9 Canonical Smiles: CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

1.10 Isomers Smiles: CC(C)/C=C/CCCCC(=O)NCC1=CC(=C(C=C1)O)OC

2. Properties

2.1 Density: 1.041g/cm3

2.1 Melting point: 62-65°C(lit.)

2.1 Boiling point: 511.5ºC at 760mmHg

2.1 Refractive index: 1.5100 (estimate)

2.1 Flash Point: 113°C

2.1 Precise Quality: 305.19900

2.1 PSA: 58.56000

2.1 logP: 4.18050

2.1 Solubility: H2O: insoluble

2.2 Appearance: Solid

2.3 Chemical Properties: N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide has a mild, warm-herbaceous odor and burning, pungenttaste (10 ppm). It is used in compounded flavors for sauces where the pungent note is desired.

2.4 Color/Form: Powder

2.5 Odor: Highly volatile with a pungent odor

2.6 pKa: 9.76±0.20(Predicted)

2.7 Water Solubility: H2O: insoluble ;soluble in petroleum ether. Slightly soluble in concentrated hydrochloric acid

2.8 Spectral Properties: MAX ABSORPTION (ALCOHOL): 227 NM (LOG E= 3.91); 281 NM (LOG E= 3.43)
IR: 17226 (Sadtler Research Laboratories IR Grating Collection)
UV: 2-581 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
UV max: 227, 281 nm (epsilon 7000, 2500)

2.9 Stability: Stable. Incompatible with strong oxidizing agents.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 History: Capsaicin is a naturally occurring substance that is responsible for the burning, pungent sensation associated with the ingestion of hot peppers from the Capsicum genus. The effect elicited by these peppers is at the origin of the name Capsicum, which derives from the Greek kapto, meaning “to bite”.Hot peppers are a native plant from the American tropics and their use can be traced back to the Aztec and Inca civilizations. The Aztecs named them “chilies” and used them for culinary purposes. After discovery of the New World, chili pods were introduced in Europe and their cultivation expanded to other parts of the globe. Nowadays, hot peppers are found in nearly every country and are an important part of the culinary tradition of many different cultures.The active component of chili peppers was initially isolated by J. C. Thresh in 1846. The compound was named “capsaicin” and its chemical structure was later determined by E. K. Nelson in 1919. The complete chemical synthesis of 8-methyl-N- vanillyl-6-nonenamide (capsaicin’s IUPAC* name) was reported in 1930 by Spath &Darling. In the 1960’s, Japanese investigators identified additional substances from Capsicum extracts with similar chemical and pharmacological properties that were termed “capsaicinoids”. Currently, this family of chemical analogues includes both natural (homodihydrocapsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin and capsaicin) and synthetic (nonivamide) members.

3.2 Potential Exposure: Botanical animal and insect repellentused to repel birds, voles, deer, rabbits, squirrels, insects,and attacking dogs. Capsaicin, which is made from theCapsicum red chili pepper can be used indoors to protectcarpets and upholstered furniture, and outdoors to protectfruit and vegetable crops, flowers, ornamental plants,shrubbery, trees, and lawns. It is also used in pepper sprayssuch as MACE, and as an analgesic in creams, lotions andsolid sticks to reduce arthritic, postoperative and neuopathicpain, such as shingles. Capsaicin is obtained by grindingdried, ripe Capsicum frutescens L. chili peppers into a finepowder. The oleoresin is derived by distilling the powderin a solvent and evaporating the solvent. The resultinghighly concentrated liquid has little odor but has anextremely pungent taste

3.3 Purification Methods: Recrystallise capcaicin from pet ether (b 40-60o), or pet ether/Et2O (9:1). Also purify it by chromatography on neutral Al2O3 (grade V) and elute successively with *C6H6, *C6H6/EtOAc (17:3) then *C6H6/EtOAc (7:3), and distil it at 120o/10-5mm, then repeatedly recrystallise the needles from isopropanol (charcoal). [Crombie et al. J Chem Soc 11025 1955, Bennett & Kirby J Chem Soc(C) 442 1968.] It causes pain and is neurotoxic [Bevan & Szolcsanyi Trends in Pharmacol Sci 11 330 1990, Beilstein 13 IV 2588].

3.4 Shipping: UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required.

3.5 Usage: Capsaicin is what makes chili peppers hot. It is an irritant.for mam- mals, but not for birds. This may be because birds spread the seeds better than mammals. It causes a burning sensation in any mam- malian tissue with which it comes in contact.Capsaicin is a nonpolar molecule; it dissolves in fats and oils, not in water. This is why water does not take away the burning sensation, but whole milk or other fat-containing liquids or foods will.As an ingredient in medicines, capsaicin is used to relieve pain from arthritis, muscle aches, and sprains. It is a rubefacient, meaning it dilates blood vessels. The heat effect overwhelms nerves, causing a localized numbing sensation.Capsaicin is also used in pepper spray.

3.6 Waste Disposal: Do not discharge into drainsor sewers. Dispose of waste material as hazardous wasteusing a licensed disposal contractor to an approved landfill.Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration witheffluent gas scrubbing is recommended. In accordancewith 40CFR165, follow recommendations for the disposalof pesticides and pesticide containers. Noncombustible containers should be crushed and buried under more than40 cm of soil. Must be disposed properly by followingpackage label directions or by contacting your local or federal environmental control agency, or by contacting yourregional EPA office Capsaicin Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Symbol: GHS06, GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R25; R37/38; R41; R42/43

4.1 Safety Statements: S22-S26-S28-S36/39-S45

4.1 Exposure Standards and Regulations: Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: capsaicin is included in fever blister and cold sore treatment drug products.

4.2 Packing Group: II

4.2 Octanol/Water Partition Coefficient: log Kow = 3.04 [LaHann TR et al; Proc West Pharmacol Soc 32: 201-4 (1989)] PubMed Abstract

4.3 Other Preventative Measures: Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.
Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

4.4 Hazard Class: 6.1(a)

4.4 Hazard Declaration: H301-H315-H317-H319-H334-H335

4.4 Cleanup Methods: If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

4.5 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

4.6 RIDADR: UN 2811 6.1/PG 2

4.6 Caution Statement: P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311

4.6 Formulations/Preparations: Formulation types registered: dry powder, liquid formulation and liquid spray ground
Trade names: Hot Pepper wax; Hot Sauce; Super Hot Pepper Guard.

4.7 Incompatibilities: Slowly hydrolyzes in water, releasingammonia and forming acetate salts.

4.8 WGK Germany: 3

4.8 RTECS: RA8530000

4.8 Protective Equipment and Clothing: Contact with products containing capsaicin produces local irritation and lacrimation.
Capsaicin is a powerful irritant; initial administration causes intense pain.
Based on the application methods and formulation types, the potential for eye, dermal and inhalation exposure to mixers, loaders and applicators does exist. In addition the potential fo post-application exposure may be significant from the foliar treatments applied prior to harvest since pre-harvest intervals are being removed from the label.

4.9 Skin, Eye, and Respiratory Irritations: Contact with products containing capsaicin produces local irritation and lacrimation.
Capsaicin is a powerful irritant; initial administration causes intense pain.
Based on the application methods and formulation types, the potential for eye, dermal and inhalation exposure to mixers, loaders and applicators does exist. In addition the potential fo post-application exposure may be significant from the foliar treatments applied prior to harvest since pre-harvest intervals are being removed from the label.

4.10 Safety: Hazard Codes of?Capsaicin (CAS NO.404-86-4):?T,T+
Risk Statements: 25-41-42/43-36/37/38?
R25: Toxic if swallowed.?
R41: Risk of serious damage to the eyes.?
R42/43: May cause sensitization by inhalation and skin contact.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-26-28-45-36/37/39?
S22: Do not breathe dust.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S28: After contact with skin, wash immediately with plenty of soap-suds.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: RA8530000
F: 10-21
HazardClass: 6.1(a)
PackingGroup: II

4.11 Specification: Off-White Crystalline Solid
usageEng:A representative lot is a 5:1 E:Z mixture. It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.
Safety Statements:22-26-28-36/39-45-36/37/39
22:Do not breathe dust
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/39:Wear suitable protective clothing and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection

4.12 Toxicity: LD50 oral in mouse: 47200ug/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

404-86-4Total: 21 Synthesis Route

502-44-3 119 Suppliers

404-86-4 386 Suppliers

Literatures:
Gannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1064 - 1071
Yield: null

121-33-5 638 Suppliers

404-86-4 386 Suppliers

Literatures:
Kaga, Harumi; Miura, Masakatsu; Orito, Kazuhiko Journal of Organic Chemistry, 1989 , vol. 54, p. 3477 - 3478
Yield: null

5631-95-8

404-86-4 386 Suppliers

Literatures:
Crombie et al. Journal of the Chemical Society, 1955 , p. 1025
Yield: null

View all

8. Precursor and Product

precursor:

59721-82-3

179617-41-5

31467-60-4

1196-92-5

59721-81-2

95636-02-5

90369-20-3

179617-47-1

179617-42-6

1221557-70-5

121-33-5

59721-83-4

59320-77-3

4547-43-7

1221557-61-4

5631-95-8

112375-54-9

90369-18-9

502-44-3

6654-36-0

93545-84-7

50889-29-7

View all

product :

112375-54-9

5129-54-4

19408-84-5

5129-53-3

9. Other Information

9.0 Description: Capsaicin is the main chemical that makes chili peppers hot. Capsaicin is an animal repellent that is also used against insects and mites. Capsaicin was first registered for use in the United States in 1962. The U.S. Environmental Protection Agency considers it to be a biochemical pesticide because it is a naturally occurring substance.

The chemical compound capsaicin (8-methyl-N-vanillyl-6-nonenamide) is the active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue it comes in contact with. Capsaicin and several related compounds are called capsaicinoids and are produced as a secondary metabolite by chili peppers, probably as deterrents against herbivores. Pure capsaicin is a hydrophobic, colorless, odorless, crystalline to waxy compound.

9.1 History: Capsaicin is a naturally occurring substance that is responsible for the burning, pungent sensation associated with the ingestion of hot peppers from the Capsicum genus. The effect elicited by these peppers is at the origin of the name Capsicum, which derives from the Greek kapto, meaning “to bite”.
Hot peppers are a native plant from the American tropics and their use can be traced back to the Aztec and Inca civilizations. The Aztecs named them “chilies” and used them for culinary purposes. After discovery of the New World, chili pods were introduced in Europe and their cultivation expanded to other parts of the globe. Nowadays, hot peppers are found in nearly every country and are an important part of the culinary tradition of many different cultures.
The active component of chili peppers was initially isolated by J. C. Thresh in 1846. The compound was named “capsaicin” and its chemical structure was later determined by E. K. Nelson in 1919. The complete chemical synthesis of 8-methyl-N- vanillyl-6-nonenamide (capsaicin’s IUPAC* name) was reported in 1930 by Spath &Darling. In the 1960’s, Japanese investigators identified additional substances from Capsicum extracts with similar chemical and pharmacological properties that were termed “capsaicinoids”. Currently, this family of chemical analogues includes both natural (homodihydrocapsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin and capsaicin) and synthetic (nonivamide) members.

9.2 Uses: Capsaicin is what makes chili peppers hot. It is an irritant.for mam- mals, but not for birds. This may be because birds spread the seeds better than mammals. It causes a burning sensation in any mam- malian tissue with which it comes in contact.
Capsaicin is a nonpolar molecule; it dissolves in fats and oils, not in water. This is why water does not take away the burning sensation, but whole milk or other fat-containing liquids or foods will.
As an ingredient in medicines, capsaicin is used to relieve pain from arthritis, muscle aches, and sprains. It is a rubefacient, meaning it dilates blood vessels. The heat effect overwhelms nerves, causing a localized numbing sensation.
Capsaicin is also used in pepper spray.

9.3 Description: Capsaicin is a terpene alkaloid that has been found in Capsicum and has diverse biological activities. It induces inward currents in HEK293 cells expressing rat transient receptor potential vanilloid 1 (TRPV1; EC₅₀ = 0.64 μM at neutral pH), an effect that can be blocked by the TRPV1 inhibitor A-425619. Capsaicin (10 and 50 μM) decreases LPS-induced prostaglandin E₂ (PGE₂; Item No. 14010) production, as well as reduces LPS- and IFN-induced nitric oxide (NO) release in isolated mouse peritoneal macrophages. Capsaicin induces substance P release in rat spinal cord slices with an EC₅₀ value of 2.3 μM. It reduces acetylcholine- or phenylquinone-induced writhing (ED₅₀s = 1.33 and 1.38 mg/kg, respectively, s.c.) but has no effect on the latency to paw withdrawal in the hot plate test in mice (ED₅₀ = >20 mg/kg, s.c.). Formulations containing capsaicin have been used in the treatment of nerve pain associated with shingles.

9.4 Description: Capsaicin has a mild, warm-herbaceous odor and a burning pungent taste (at 10 ppm). It is used in compounded flavors for sauces where the pungent note is desired. This substance is present in several species of Capsicum (Family, Solanaceae). The sensation of pain, accompanied by irritation and inflammation, is due to substance P depletion from sensory (afferent) nerve fibers. These properties are used to study the physiology of pain and the effects as a counterirritant and gastrointestinal stimulant. This substance may be prepared from 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation form cis-capsaicin, pelargonic acid vanilamide, and dihydrocapsaicin, reaction of capsaicin.

9.5 Chemical Properties: N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide has a mild, warm-herbaceous odor and burning, pungent taste (10 ppm). It is used in compounded flavors for sauces where the pungent note is desired.

9.6 Physical properties: Appearance: crystalline white powder, with highly volatile and pungent odor. Solubility: freely soluble in alcohol, ether, benzene, and chloroform; slightly soluble in carbon disulfide, petroleum, and hydrochloric acid; insoluble in water. Melting point: 65?°C.

9.7 Occurrence: The pungent principle in the fruits of various Capsicum species (Solanaceae)

9.8 History: In 1816, Christian Friedrich Bucholz (1770–1818) first carried out the purification of capsaicin. He obtained incompletely purified capsaicin and named it “capsaicin” . In 1876, John Clough Thresh (1850–1932) further purified and got pure capsaicin and named it capsaicin. In 1919, Nelson identified the capsaicin structure. In 1930, E.?Spath and S.?F. Darling used chemical synthesis method for the first time to successfully synthesize capsaicin. In 1961, the Japanese chemists S.? Kosuge and Y.? Inagaki isolated similar substances from capsicum and named them capsaicinoids.
More than 14 capsaicin homologues have been found till now, the structures are similar with capsaicin, and the typical structure is H3CO(HO)-C6H3-CH2-NHCO-R, which is only different from R group. Capsaicin is the highest content in chili pepper. Capsaicin and dihydrocapsaicin are the most potent active substances in capsicum. Capsaicin and its analogues have been synthesized in large quantities in practice and can be used not only in medicine but also in agriculture and industry. Although there is a long history of pharmacological and chemical studies on capsaicin, until November 16, 2009, the US Food and Drug Administration (FDA) approved the first containing high concentration capsaicin prescription Qutenza (8% capsaicin) patch for the treatment of postherpetic neuralgia. At present, most countries have capsaicin prescription drugs on market, but clinical indications are limited in the treatment of pain.

9.9 Indications: Capsaicin (Zostrix) is approved for the relief of pain following herpes zoster infection (postherpetic neuralgia). The drug depletes neurons of substance P, an endogenous neuropeptide that may mediate cutaneous pain. It is applied to affected skin after open lesions have healed. Local irritation is common.

9.10 General Description: Capsaicin occurs as the active ingredient of hot/red pepper and was first obtained by Thresh in 1846. It is a lipophilic vanilloid compound responsible for the acrid taste of hot peppers.

9.11 Merck: 14,1768

9.12 BRN: 2816484

9.13 Application in Particular Diseases

In Osteoarthritis:

Capsaicin, an extract of red peppers that causes release and ultimately depletion of substance P from nerve fibers, has been beneficial in providing pain relief in OA when applied topically over affected joints. It may be used alone or in combination with oral analgesics or NSAIDs.
To be effective, capsaicin must be used regularly, and it may take up to 2 weeks to work. It is well tolerated, but some patients experience temporary burning or stinging at the site of application. Patients should be warned not to get the cream in their eyes or mouth and to wash their hands after application.
Application of the cream, gel, or lotion is recommended four times daily, but tapering to twice-daily application may enhance long-term adherence with adequate pain relief.

9.14 Chemical Properties: Off-White Crystalline Solid

9.15 Chemical Properties: Crystalline solid, rectangular plates, or scales. Pungent odor and burning taste.

9.16 Uses: A representative lot is a 5:1 E:Z mixture. It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

9.17 Uses: K channel blocker; multiple sclerosis therapy

9.18 Uses: analgesic (topical), depletes Substance P, neurotoxic

9.19 Uses: Capsaicin analogue (C175680). It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

9.20 Uses: Capsaicin is used in many topical ointments used to relieve the pain of peripheral neuropathy (treatment of pain in the nerve endings near the surface of the skin).

9.21 Uses: As a tool in neurobiological research.

9.22 Biological Activity: Prototypic vanilloid receptor agonist (pEC 50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptive and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset? .

9.23 Potential Exposure: Botanical animal and insect repellent used to repel birds, voles, deer, rabbits, squirrels, insects, and attacking dogs. Capsaicin, which is made from the Capsicum red chili pepper can be used indoors to protect carpets and upholstered furniture, and outdoors to protect fruit and vegetable crops, flowers, ornamental plants, shrubbery, trees, and lawns. It is also used in pepper sprays such as MACE, and as an analgesic in creams, lotions and solid sticks to reduce arthritic, postoperative and neuopathic pain, such as shingles. Capsaicin is obtained by grinding dried, ripe Capsicum frutescens L. chili peppers into a fine powder. The oleoresin is derived by distilling the powder in a solvent and evaporating the solvent. The resulting highly concentrated liquid has little odor but has an extremely pungent taste

9.24 First aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

9.25 Shipping: UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

9.26 Purification Methods: Recrystallise capcaicin from pet ether (b 40-60o), or pet ether/Et2O (9:1). Also purify it by chromatography on neutral Al2O3 (grade V) and elute successively with *C6H6, *C6H6/EtOAc (17:3) then *C6H6/EtOAc (7:3), and distil it at 120o/10-5mm, then repeatedly recrystallise the needles from isopropanol (charcoal). [Crombie et al. J Chem Soc 11025 1955, Bennett & Kirby J Chem Soc(C) 442 1968.] It causes pain and is neurotoxic [Bevan & Szolcsanyi Trends in Pharmacol Sci 11 330 1990, Beilstein 13 IV 2588].

9.27 Incompatibilities: Slowly hydrolyzes in water, releasing ammonia and forming acetate salts.

9.28 Waste Disposal: Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Noncombustible containers should be crushed and buried under more than 40 cm of soil. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office

10. Computational chemical data

Molecular Weight: 305.41200g/mol
Molecular Formula: C₁₈H₂₇NO₃
Compound Is Canonicalized: True
XLogP3-AA: 3.6
Exact Mass: 305.19909372
Monoisotopic Mass: 305.19909372
Complexity: 341
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 58.6
Heavy Atom Count: 22
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB6MAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAQCAAADQTBmAYyBoLABgCIAiFSEACCCAAgIAAIiIEOjIgNJjKGsRuEcCtk1hGLuAe42BIOIAABAAAAQABAAAIAAACAAAAAAAAAAA==

11. Question & Answer

Are there other chemicals that give false pain effects, like for example, how capsaicin gives a false signal/sense of burning to our body despite our body being actually fine? Apr 16 2022
There are many of them. Ever see jelly style paint stripper? Based on methylene chloride. As a teen I got paint on my hands, so I glopped some on there to take the paint off. PAIN! Severe AGONY! Hands felt like I was holding them in a fire! Hurt so bad I had trouble breathing. CN and CS teargas als...
What is pure capsaicin? Apr 16 2022
Capsaicin is the hot-tasting component of Capsicum fruits (variously referred to as chilies, chili peppers, cayenne, paprika, aji, pimento, etc.), where it is present at levels up to 1% by dry weight [Arceo et al., 1995]. Several homologues have been isolated from peppers, but the principal form is...
How does casein (the protein found in milk) help against capsaicin (a spicy chemical)? Nov 21 2021
Its the fat in milk that cools a pepper burn. Your right though. Even non fat milk helps. Chewing a piece of bread also helps.
Is there a specific chemical reaction between capsaicin and casein? Is there a stoichiometric relationship between them? [closed] Nov 06 2021
I rather doubt that there's a significant binding between capsaicin and the protein casein or a stoichiometric reaction. If you look at the structure of capsaicin, you'll recognize that it's a rather unpolar molecule. With other words, it is hardly soluble in water, but will dissolve in oil. This i...

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