ChemicalBook > CAS DataBase List > L-Menthol

L-Menthol

Product Name
L-Menthol
CAS No.
2216-51-5
Chemical Name
L-Menthol
Synonyms
MENTHOL;Menthol Crystals;(-)-MENTHOL;DL-Menthol menthol crystal extract;(1R,2S,5S)-2-ISOPROPYL-5-METHYL-CYCLOHEXANOL;NATURAL MENTHOL;Mentol Crystal;(R)-(-)-Menthol;L-MENTOL;L(-)-MENTHOL
CBNumber
CB7390694
Molecular Formula
C10H20O
Formula Weight
156.27
MOL File
2216-51-5.mol
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L-Menthol Property

Melting point:
41-45 °C (lit.)
alpha 
-51 º (589nm, c=10, EtOH)
Boiling point:
212 °C (lit.)
Density 
0.89 g/mL at 25 °C (lit.)
vapor pressure 
0.8 mm Hg ( 20 °C)
refractive index 
1.46
FEMA 
2665 | MENTHOL RACEMIC
Flash point:
200 °F
storage temp. 
Store below +30°C.
solubility 
490mg/l
form 
Crystals or Crystalline Needles
pka
15.30±0.60(Predicted)
Specific Gravity
0.89
color 
Colorless to white
Odor
at 10.00 % in dipropylene glycol. peppermint cooling mentholic minty
Odor Type
mentholic
optical activity
[α]22/D 49°, c = 10 in 95% ethanol
Water Solubility 
insoluble
Merck 
14,5837
BRN 
1902293
Dielectric constant
3.2（Ambient）
Stability:
Stable.
InChIKey
NOOLISFMXDJSKH-KXUCPTDWSA-N
LogP
3.15 at 25℃
CAS DataBase Reference
2216-51-5(CAS DataBase Reference)
NIST Chemistry Reference
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1«alpha»,2«beta»,5«alpha»)]-(2216-51-5)
EPA Substance Registry System
Levomenthol (2216-51-5)
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Safety

Hazard Codes 
Xi
Risk Statements 
37/38-41-36/37/38
Safety Statements 
26-39-37/39-36
WGK Germany 
2
RTECS 
OT0700000
TSCA 
Yes
HS Code 
29061100
Hazardous Substances Data
2216-51-5(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 3300 mg/kg LD50 dermal Rabbit > 5000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W266590
Product name
L-Menthol
Purity
≥99%, FCC, FG
Packaging
1kg
Price
$130
Updated
2024/03/01
Sigma-Aldrich
Product number
W266590
Product name
L-Menthol
Purity
≥99%, FCC, FG
Packaging
4kg
Price
$427
Updated
2024/03/01
Sigma-Aldrich
Product number
W266590
Product name
L-Menthol
Purity
≥99%, FCC, FG
Packaging
25kg
Price
$2250
Updated
2024/03/01
Sigma-Aldrich
Product number
W266523
Product name
L-Menthol
Purity
natural, ≥99%, FCC, FG
Packaging
100g
Price
$81.9
Updated
2024/03/01
Sigma-Aldrich
Product number
W266523
Product name
L-Menthol
Purity
natural, ≥99%, FCC, FG
Packaging
1kg
Price
$163
Updated
2024/03/01
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L-Menthol Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

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.

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.

Definition

ChEBI: A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.

Acquired resistance

(1R,2S,5R)-(-)-Menthol (L-Menthol) is the natural form of Menthol. L- and D-menthol are variants of the same molecule, but have a mirror-image structure in relation to each other, like the right and left hand.

General Description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Flammability and Explosibility

Non flammable

Biological Activity

l-Menthol inhibite the binding of 13 ligands (calcium channels, sodium channels, γ-aminobutyric acid type A (GABAA) receptor, GABA transporter, dopamine transporter, dopamine D4 receptor, adenosine A2a receptor, α2A-adrenergic receptor, histamine H2 receptor, bombesin receptor, angiotensin AT1 receptor, vasopressin V2 receptor, and leukotriene B4 receptor) with relatively high inhibition rates and acts on these ligands over a similar concentration range. It acts as a positive allosteric modulator of the GABAA receptor rather than an agonist. In periaqueductal grey neurons in rat midbrain slices, l-menthol was shown to prolong spontaneous GABAA receptor–mediated inhibitory current, most likely via a mechanism distinct from that of benzodiazepines. It acts on the dopamine D4 receptor and the dopamine transporter. l-menthol inhibits the [3H]-WIN35,428 binding, similar to GBR12909, suggesting that l-menthol inhibits the binding of dopamine to the dopamine transporter and leading to decreased dopamine uptake[1].

Biochem/physiol Actions

Taste at 25 ppm

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.

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.]

References

[1] Umezu T, et al. Identification of novel target molecules of l-menthol. Heliyon, 2021; 7: e07329.

L-Menthol Preparation Products And Raw materials

Raw materials

Petroleum crude oil ISOPULEGOL, TECH. PEPPERMINT L-MENTHONE Citronellal NEOMENTHOL, (-)-(SG) Cornmint oil Thymol DL-Menthol m-Cresol

Preparation Products

(R,R)-DIPAMP (-)-MENTHOXYACETIC ACID
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L-Menthol Suppliers

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View Lastest Price from L-Menthol manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Menthol / L-Menthol 2216-51-5
Price
US $180.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-30
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
L-Menthol 2216-51-5
Price
US $500.00-300.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-23
Chongqing Zhihe Biopharmaceutical Co., Ltd.
Product
L-Menthol 2216-51-5
Price
US $0.00-0.00/kg
Min. Order
0.10000000149011612kg
Purity
99%
Supply Ability
20tons
Release date
2023-12-21

2216-51-5, L-MentholRelated Search:

ISOPROPYL LAURATE ISOPULEGOL, TECH. 2-Methylcyclohexanol METHYLCYCLOHEXANOL Cyclohexanone Cyclohexene (+)-ISOMENTHOL (1S)-(+)-mentho 1-Methylcyclohexanol Cyclohexanol Propylthiouracil Cyclohexylamine Molasses Isopropyl alcohol (+)-NEOMENTHOL Peppermint oil (2R,5S)-5-(5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester 5-fluoro-1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)cytosine Menthol Crystals

  • (1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol
  • (1r,3r,4s)-(-)-mentho
  • (1R,3R,4S)-(-)-MENTHOL
  • (R)-(-)-Menthol
  • Emtricitabine Impurity 31
  • Natural Menthol Crystal
  • L-Meng alcohol Natural menthol Menthol (L)
  • DL-Menthol menthol crystal extract
  • (-)-Menthol【(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol】
  • (1S,2R,5S)-5-methyl-2-propan-2-yl-1-cyclohexanol
  • water soluble mentholin
  • Menthol, Crystal, FCC
  • Menthol (250 mg)
  • Mentol Crystal
  • Menthol ,natura
  • L-Menthol ,99.5%
  • 5-(1-methyl ethyl)cyclohexano1
  • L-Menthol ,99.50%
  • [1R,2S,5R,(-)]-2-Isopropyl-5-methylcyclohexan-1-ol
  • Methylpropylphenylhexahydride
  • (-)-trans-p-Methan-cis-3-ol
  • NATURAL MENTHOL
  • FEMA 2665
  • (-)-MENTHOL
  • MENTHOL
  • MENTHOL, (-)-
  • LEVO-MENTHOL
  • LEVOMENTHOLUM
  • L-P-MENTHAN-3-OL
  • L-MENTHAN-3-OL
  • (-)-L-MENTHOL
  • L(-)-MENTHOL
  • L-MENTHOL
  • L-MENTHOL (NATURAL)
  • L-2-ISOPROPYL-5-METHYLCYCLOHEXANOL
  • L-4-MENTHAN-3-OL
  • L(-)-Menthol /(1R,2S,5R)-(-)-Menthol
  • L-MENTHOL (PELLETS) SYNTH.
  • L-MENTHOL CRYSTALS USP (NATURAL)
  • Menthol, L-
  • (-)-Menthol, (1R,2S,5R)-(-)-Menthol, 5-Methyl-2-(1-methylethyl)cyclohexanol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
  • (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol
  • (-)-Menthol, 5-Methyl-2-(1-methylethyl)cyclohexanol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
  • L-Menthol crystals
  • (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol, Levomentholum
  • L(-)-Menthol, 99.7% 100GR
  • L(-)-Menthol, 99.7% 500GR
  • 5-methyl-2-(1-methylethyl)-,(1r-(1alpha,2beta,5alpha))-cyclohexano
  • 5-methyl-2-(1-methylethyl)-,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol
  • 5-methyl-2-(1-methylethyl)-,[1theta-(1alpha,2beta,5alpha)]-cyclohexano
  • Cyclohexanol,5-methyl-2-(1-methylethyl)-,[1R-(1.alpha.,2.beta.,5.alpha.)]-
  • Menthol, (1R,3R,4S)-(-)-
  • U.s.p. menthol
  • u.s.p.menthol
  • uspmenthol
  • 1-P-MENTHAN-3-OL
  • (1R,2S,5R)-(-)-MENTHOL
  • (1R,2S,5R)-MENTHOL