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L-Menthol structure
L-Menthol structure

L-Menthol

Iupac Name:(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
CAS No.: 2216-51-5
Molecular Weight:156.2652
Modify Date.: 2022-11-08 00:44
Introduction: (-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1]. View more+
1. Names and Identifiers
1.1 Name
L-Menthol
1.2 Synonyms

(&minus)-menthol (&minus)-Menthol,(1R,2S,5R)-(&minus)-Menthol,(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (&minus)-Menthol,(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol,5-Methyl-2-(1-methylethyl)cyclohexanol (-)-(1R,2S,5R)-Menthol (-)-(1R,3R,4S)-Menthol (-)-Menthol (-)-MENTHYL ALCOHOL (-)-p-Menthan-3-ol (-)-trans-p-Methan-cis-3-ol (1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol (1R)-(-)-Menthol (1R,2S,5R)-(&minus)-Menthol (1R,2S,5R)-(-)-Menthol (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (5-Methyl-2-(1-methylethyl)cyclohexanol (1R,2S,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-ol (1r,3r,4s)-(-)-mentho (1R,3R,4S)-(-)-MENTHOL (R)-(-)-Menthol [1R-(1a,2b,5a)]-5-Methyl-2-(1-methylethyl)cyclohexanol Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- DL-Menthol DL-Menthol menthol crystal extract EINECS 218-690-9 Emtricitabine Impurity 31 L(-)-Menthol Levomenthol levo-menthol L-Meng alcohol Natural menthol Menthol (L) L-MentholuM Menthol Menthol, l- MFCD00062979 Minclea Natural Menthol Crystal UNII:YS08XHA860 uspmenthol

1.3 CAS No.
2216-51-5
1.4 CID
16666
1.5 EINECS(EC#)
218-690-9
1.6 Molecular Formula
C10H20O (isomer)
1.7 Inchi
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
1.8 InChkey
NOOLISFMXDJSKH-KXUCPTDWSA-N
1.9 Canonical Smiles
CC1CCC(C(C1)O)C(C)C
1.10 Isomers Smiles
C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
2. Properties
3.1 Density
0.89
3.1 Melting point
41-43℃
3.1 Boiling point
212℃
3.1 Refractive index
1.46
3.1 Flash Point
93℃
3.2 Precise Quality
156.15100
3.2 PSA
20.23000
3.2 logP
2.43950
3.2 Solubility
490mg/l
3.3 VaporDensity
5.4 (NTP, 1992) (Relative to Air)
3.4 Appearance
white crystals
3.5 Storage
Ambient temperatures.
3.6 Chemical Properties
white to light yellow crystal powde
3.7 Color/Form
Powder
3.8 Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.
3.9 Odor
Peppermint odor
3.10 pKa
15.30±0.60(Predicted)
3.11 Water Solubility
insoluble
3.12 Spectral Properties
Index of refraction: 1.58 @ 25 deg C/D; Specific optical rotation: -50 deg @ 18 deg C/D (10% alc soln) /D- form/
MASS: 966 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
3.13 Stability
Stable.
3.14 StorageTemp
Store below +30°C.
3. Use and Manufacturing
4.1 Definition
ChEBI: A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.
4.2 Purification Methods
Crystallise menthol from CHCl3,pet ether or EtOH/water. [Barrow & Atkinson J Chem Soc 638 1939, Beilstein 6 III 133, 6 IV 150.] L-Menthol Preparation Products And Raw materials Raw materials
4.3 Usage
analgesic (topical), antipruritic agent
4. Safety and Handling
5.1 Symbol
GHS07;
5.1 Hazard Codes
Xi
5.1 Signal Word
Warning
5.1 Risk Statements
R36/37/38;R41
5.1 Safety Statements
S26;S37/39
5.1 Exposure Standards and Regulations
Essential oils, oleoresins (solvent-free), and natural extractives (including distillates) that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Menthol is included on this list.
5.2 Octanol/Water Partition Coefficient
log Kow = 3.3
5.3 Hazard Declaration
H315; H319
5.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.4 RIDADR
NONH for all modes of transport
5.4 FirePotential
FIRE HAZARD: SLIGHT
Combustible liquid.
5.5 Safety Profile
Poison by intravenous route. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An eye irritant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
5.6 Caution Statement
P261-P280-P305 + P351 + P338
5.6 Formulations/Preparations
SOME SYNTHETIC MENTHOLS ARE NOT CHEMICAL INDIVIDUALS BUT...MIXTURES OF VARIOUS ISOMERS...THESE ARE DESIGNATED...L-MENTHOL, DL-MENTHOL, L-ISOMENTHOL, D-ISOMENTHOL, DL-ISOMENTHOL, L-NEOMENTHOL, D-NEOMENTHOL, L-NEOISOMENTHOL, D-NEOISOMENTHOL AND DL-NEOISOMENTHOL.
WHEN MIXED WITH ABOUT EQUAL WT OF CAMPHOR, CHLORAL HYDRATE, PHENOL, OR THYMOL, MENTHOL FORMS "EUTECTIC" MIXT LIQUIFYING @ ROOM TEMP.
MENTHOL, USP DRUG MARKETED UNDER GENERIC NAME.
Grades: Technical; USP; FCC
Synthetic menthol is available as the optically active levo-menthol with a purity of 99.9%. Synthetic menthol is also commercially available as the racemic mixture
/Present in/ cigarettes and pipe tobacco (0.1-0.45%) shaving creams, pre- and aftershave lotions (0.2-0.3%); toothpastes (0.5%); mouthwashes (1-2%); chewing gums (0.5%); cough drops (0.1%); refreshing towels (1%); rubbing alcohol (1-1.2%); and shampoos (2-0.5%)
Mentholatum Deep Heating Rub /contains/ 5.9% Menthol; Mentholatum ointment, 1.35%; Mentholatum Deep Heating Lotion, 6%
5.7 WGK Germany
2
5.7 RTECS
OT0700000
5.7 Protective Equipment and Clothing
MODERATE IRRITANT TO MUCOUS MEMBRANES ON INHALATION.
5.8 Reactivities and Incompatibilities
Incompatible with phenol; beta-naphthol; resorcinol or thymol in trituration; potassium permanganate; chromium trioxide; pyrogallol.
5.9 Skin, Eye, and Respiratory Irritations
MODERATE IRRITANT TO MUCOUS MEMBRANES ON INHALATION.
5.10 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OT0700000
CHEMICAL NAME :
l-Menthol
CAS REGISTRY NUMBER :
2216-51-5
LAST UPDATED :
199701
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C10-H20-O
MOLECULAR WEIGHT :
156.30
WISWESSER LINE NOTATION :
L6TJ AY1&1 DQ D1 -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
34 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
DNA repair
TEST SYSTEM :
Bacteria - Bacillus subtilis
DOSE/DURATION :
10 mg/disc
REFERENCE :
OIGZDE Osaka-shi Igakkai Zasshi. Journal of Osaka City Medical Association. (Osaka-shi Igakkai, c/o Osaka-shiritsu Daigaku Igakubu, 1-4-54 Asahi-cho, Abeno-ku, Osaka, 545, Japan) V.24- 1975- Volume(issue)/page/year: 34,267,1985 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6896 No. of Facilities: 499 (estimated) No. of Industries: 5 No. of Occupations: 27 No. of Employees: 43996 (estimated) No. of Female Employees: 34625 (estimated)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

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.

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
L-Menthol is used as a cooling agent that strongly activates TRPM8.(Transient Receptor Potential Cation Channel, Subfamily M, Member 8 is a Protein Coding gene). It is used as analgesic (topical), antipruritic agent. It is used as: refreshing agent, food flavor, cool and antipruritic drug, carminative drug. Menthol crystals is used for pers onal care and cosmetics.
9.1 Merck
14,5837
9.2 BRN
1902293
9.3 Chemical Properties
white to light yellow crystal powde
9.4 Uses
(1R,2S,5R)-(-)-Menthol (L-Menthol) is the natural form of Menthol. L-Menthol is used as: refreshing agent, food flavor, cool and antipruritic drug, carminative drug. Menthol crystals is used for pers onal care and cosmetics.
9.5 Definition
ChEBI: A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.
9.6 General Description
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.
10. Computational chemical data
  • Molecular Weight: 156.2652g/mol
  • Molecular Formula: C10H20O
  • Compound Is Canonicalized: True
  • XLogP3-AA: 3
  • Exact Mass: 156.151415257
  • Monoisotopic Mass: 156.151415257
  • Complexity: 120
  • Rotatable Bond Count: 1
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Topological Polar Surface Area: 20.2
  • Heavy Atom Count: 11
  • Defined Atom Stereocenter Count: 3
  • 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: AAADceBwIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAAAAAAAGgAACAAADRSggAICAAAAAgAAAAAAAAAAAAAAAAAAAAAAAAAAEAIAAAAAQAAEAAAAAAGAwPAOgAAAAAAAAACAAAIAABAAAAAAAAAAAA==
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