Valeric acid

Iupac Name：pentanoic acid

Molecular Weight：102.13200

Modify Date.: 2023-02-03 10:05

Introduction: Valeric acid (also pentanoic acid) is a straight chain alkyl carboxylic acid.Valeric acid is mainly used for the synthesis of its esters used in foods, perfume, and cosmetics. Valeric acid is used as an intermediate for applications including ester type lubricants (in aviation turbine oils, fire-resistance hydraulic fluids, and refrigerator oils), plasticizers (dipropyl heptyl phthalate), vinyl stabilizers, and specialty chemicals. It is also used as an odorant in pesticide formulations for use on crops. View more+

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1. Names and Identifiers

1.1 Name: Valeric acid
1.2 Synonyms: 3-(methylsulfanyl)propanoic acid EINECS 203-677-2 MFCD00004413 N-PENTANOIC ACID N-VALERIC ACID N-Valeric Acid(Pentanoic Acid) N-VALERICACID(PENTANOICACID) PENTANE ACID PENTANOIC ACID PENTANOIC ACID (VALERIC) PENTANOIC ACID 100 ML PENTANOIC ACID FOR SYNTHESIS PENTANOIC-2,2-D2 ACID PROPYLACETIC ACID RARECHEM AL BO 0179 VALERIC ACID(SG) Valeric Acid, Reagent VALERIC ACID/PENTANOIC ACID VALERICACID

1.3 CAS No.: 109-52-4

1.4 CID: 7991

1.5 EINECS(EC#): 203-677-2

1.6 Molecular Formula: C5H10O2 (isomer)

1.7 Inchi: InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)

1.8 InChkey: NQPDZGIKBAWPEJ-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCCC(=O)O

1.10 Isomers Smiles: CCCCC(=O)O

2. Properties

2.1 Density: 0.939g/mLat 25°C(lit.)

2.1 Melting point: ?20-?18°C(lit.)

2.1 Boiling point: 110-111°C10mm Hg(lit.)

2.1 Refractive index: n20/D 1.408(lit.)

2.1 Flash Point: 192°F

2.2 Precise Quality: 102.06800

2.2 PSA: 37.30000

2.2 logP: 1.26120

2.2 Solubility: 40g/l

2.3 VaporDensity: 3.5 (vs air)

2.4 Appearance: Clear, pale beige liquid

2.5 Storage: Ambient temperatures.

2.6 Chemical Properties: Valeric acid has an unpleasant odor and flavor, similar to butyric acid. May consist of one or a mixture of isomers ofn-pentanoic acid and/or 2- or 3-methyl-butanoic acid.

2.7 Color/Form: Powder

2.8 Odor Threshold: 0.000037ppm

2.9 PH: 2.7 (40g/l, H2O, 20℃)

2.10 pKa: 4.84(at 25℃)

2.11 Water Solubility: 40 g/L (20 oC)

2.12 Spectral Properties: Index of refraction: 1.4086 at 20 degC/D
SADTLER REF NUMBER: 304 (IR, PRISM); 10844 (IR, GRATING)
IR: 1275 (Coblentz Society Spectral Collection)
NMR: 5995 (Sadtler Research Laboratories Spectral Collection)
MASS: 1196 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)

2.13 Stability: Stable under normal temperatures and pressures.

2.14 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: A straight-chain saturated fatty acid containing five carbon atoms.

3.2 Purification Methods: Water is removed from the acid by distillation using a Vigreux column (p 11), until the boiling point reaches 183o. A few crystals of KMnO4 are added, and after refluxing, the distillation is continued. [Andrews & Keefer J Am Chem Soc 83 3708 1961, Beilstein 2 H 299, 2 I 130, 2 II 263, 2 III 663, 2 IV 868.] Valeric acid Preparation Products And Raw materials Raw materials

3.3 Usage: valeric acid is obtained from valerian extract, which is considered skin conditioning.

4. Safety and Handling

4.1 Symbol: GHS05, GHS07

4.1 Hazard Codes: C

4.1 Signal Word: Danger

4.1 Risk Statements: R34; R52/53

4.1 Safety Statements: S26-S36-S45-S61

4.1 Exposure Standards and Regulations: Pentanoic acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow = 1.39

4.3 Fire Hazard: Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.

4.4 Other Preventative Measures: Strict precautions are necessary in handling ... any skin or eye splashes irrigated with copious amounts of water. /Saturated monocarboxylic acids/

4.5 Hazard Class: 8

4.5 Hazard Declaration: H302-H314-H412

4.5 Cleanup Methods: Collect leaking liquid in covered containers. Wash away spilled liquid with plenty of water. Do NOT let this chemical enter the environment.

4.6 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.

4.7 RIDADR: UN 3265 8/PG 3

4.7 FirePotential: Combustible liquid.

4.8 Safety Profile: Moderately toxic byingestion, intravenous, and subcutaneousroutes. Mildly toxic by inhalation. Acorrosive irritant to skin, eyes, and mucousmembranes. Combustible liquid. Whenheated to decomposition it emits acridsmoke and irritating fumes. Used inperfumes.

4.9 Caution Statement: P273-P280-P301 + P312 + P330-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

4.9 Formulations/Preparations: Grades: Technical; reagent.

4.10 WGK Germany: 1

4.10 RTECS: YV6100000

4.10 Safety: Hazard Codes:C
Risk Statements:34-52/53
34:Causes burns
52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements:26-36-45-61
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
61:Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR:UN 3265 8/PG 3
WGK Germany:1
HazardClass:8
PackingGroup:III
HS Code:29156090
Hazardous Substances Data:109-52-4(Hazardous Substances Data)

4.11 Specification: clear colorless to pale yellow liquid
usageEng:Sex attractant of the sugar beet wireworm, Limonius californicus.1
Safety Statements:26-36-45-61
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
61:Avoid release to the environment. Refer to special instructions safety data sheet

4.12 Toxicity: Corrosive. Very destructive to tissues of the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, nausea and vomiting. Extremely destructive to skin. May be absorbed through the skin.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage H412 Harmful to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

Mass spectrum (electron ionization)

7. Synthesis Route

109-52-4Total: 103 Synthesis Route

71-41-0 92 Suppliers

2173-56-0 33 Suppliers

109-52-4 80 Suppliers

Literatures:
Chemistry Letters, , # 10 p. 871 - 872
Yield: ~83%

71-41-0 92 Suppliers

31080-39-4 6 Suppliers

109-52-4 80 Suppliers

Literatures:
DE503009 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 251
Yield: null

71-41-0 92 Suppliers

638-49-3 12 Suppliers

628-63-7 133 Suppliers

109-52-4 80 Suppliers

Literatures:
Chemical Communications, , # 17 p. 2256 - 2258
Yield: null

View all

8. Other Information

8.0 Usage: Valeric acid, is used as a sex attractant of the sugar beet wireworm, Limonius californicus. It is used predominantly as an intermediate in the manufacture of flavors and perfumes, ester type lubricants, plasticizers and vinyl stabilizesrs. It is a food additive used as a synthetic flavoring substance dan adjuvant. It is an inert ingredient in controlling pest.

8.1 Merck: 14,9904

8.2 BRN: 969454

8.3 Description: Valeric acid (also pentanoic acid) is a straight chain alkyl carboxylic acid.
Valeric acid is mainly used for the synthesis of its esters used in foods, perfume, and cosmetics. Valeric acid is used as an intermediate for applications including ester type lubricants (in aviation turbine oils, fire-resistance hydraulic fluids, and refrigerator oils), plasticizers (dipropyl heptyl phthalate), vinyl stabilizers, and specialty chemicals. It is also used as an odorant in pesticide formulations for use on crops.

8.4 References: [1] http://www.chemicalland21.com
[2] Patent CA 2496307 C: High viscosity synthetic ester lubricant base stock
[3] https://www.icis.com
[4] Christopher G. Morris (1992) Academic Press Dictionary of Science and Technology

8.5 Description: Valeric acid, or pentanoic acid, is a straight - chain alkyl carboxylic acid with the chemical formula C₅H₁₀O₂. Like other lowmolecular- weight carboxylic acids, it has a very unpleasant odor. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.
Valeric acid appears similar in structure to GHB and the neurotransmitter GABA in that it is a short-chain carboxylic acid, although it lacks the alcohol and amine functional groups that contribute to the biological activities of GHB and GABA, respectively. It differs from valproic acid simply by lacking a 3- carbon side - chain.

8.6 Chemical Properties: Valeric acid has an unpleasant odor and flavor, similar to butyric acid. May consist of one or a mixture of isomers of n-pentanoic acid and/or 2- or 3-methyl-butanoic acid.

8.7 Chemical Properties: Colorless liquid; penetrating odor and taste. Soluble in water, alcohol and ether. Undergoes reactions typical of normal monobasic organic acids. Combustible.

8.8 Occurrence: The acid is not too common in nature; reported (as the corresponding ester) found in the essential oil of Boronia anemonifolia, in pineapple fruits and in other plants; also identified as acid or the corresponding ester in the essential oil of lemon petitgrain. Also reported found in apple, apple juice, banana, orange juice, bilberry, cranberry, strawberry, raspberry, papaya, grapes, celery, onion, baked potato, tomato, corn mint oil, breads, cheeses, milk, yogurt, butter, cheddar cheese, lean and fatty fish, fish oil, cooked meats, hop oil, beer, rum, whiskies, grape wines, cocoa, tea, roasted filberts, peanuts and pecans, honey, soybeans, coconut meat and milk, cloudberry, passion fruit, starfruit, trassi, mango, jackfruit, licorice, calamus, sake, buckwheat, watercress, laurel, peated malt, wort, kiwifruit, loquat, Bourbon vanilla, shrimps, oyster, scallop, cape gooseberry, sea buckthorn, Chinese quince and maté.

8.9 Uses: valeric acid is obtained from valerian extract, which is considered skin conditioning.

8.10 Uses: Sex attractant of the sugar beet wireworm, Limonius californicus.1

8.11 Definition: ChEBI: A straight-chain saturated fatty acid containing five carbon atoms.

8.12 Preparation: By oxidation of n-amyl alcohol or, together with other isomers, by distillation of valerian roots; also by reacting butyl bromide and sodium cyanide with subsequent saponification of the formed butyl nitrile.

8.13 Aroma threshold values: Detection: 940 ppb to 3 ppm

8.14 Taste threshold values: Taste characteristics at 100 ppm: acidic, dairy-like with milky and cheese nuances.

8.15 Synthesis Reference(s): Synthetic Communications, 26, p. 165, 1996 DOI: 10.1080/00397919608003877
Tetrahedron Letters, 31, p. 1257, 1990 DOI: 10.1016/S0040-4039(00)88779-1
Tetrahedron, 40, p. 3635, 1984 DOI: 10.1016/S0040-4020(01)88794-9

8.16 General Description: A colorless liquid with a penetrating unpleasant odor. Density 0.94 g / cm3. Freezing point -93.2°F (-34°C). Boiling point 365.7°F (185.4°C). Flash point 192°F (88.9°F). Corrosive to metals and tissue.

8.17 Air & Water Reactions: Water soluble.

8.18 Reactivity Profile: Valeric acid is a carboxylic acid. Exothermically neutralizes bases, both organic and inorganic, producing water and a salt. Can react with active metals to form gaseous hydrogen and a metal salt. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts with sulfites, nitrites, thiosulfates and dithionites to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May catalyze (increase the rate of) chemical reactions.

8.19 Health Hazard: Corrosive. Very destructive to tissues of the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, nausea and vomiting. Extremely destructive to skin. May be absorbed through the skin.

8.20 Fire Hazard: Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.

8.21 Safety Profile: Moderately toxic by ingestion, intravenous, and subcutaneous routes. Mildly toxic by inhalation. A corrosive irritant to skin, eyes, and mucous membranes. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. Used in perfumes.

8.22 Purification Methods: Water is removed from the acid by distillation using a Vigreux column (p 11), until the boiling point reaches 183o. A few crystals of KMnO4 are added, and after refluxing, the distillation is continued. [Andrews & Keefer J Am Chem Soc 83 3708 1961, Beilstein 2 H 299, 2 I 130, 2 II 263, 2 III 663, 2 IV 868.]

9. Computational chemical data

Molecular Weight: 102.13200g/mol
Molecular Formula: C₅H₁₀O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 102.068079557
Monoisotopic Mass: 102.068079557
Complexity: 59.1
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACACAgAACCAAAAgAIAACQCAAAAAAAAAAAAAEAAAAAABIAAAAAQAAEAAAAAACIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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