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MedKoo Cat#: 596450 | Name: Levomenthol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levomenthol is the principal component of peppermint oil. It is widely used in confectionaries cosmetics and toothpaste for its characteristic peppermint flavor and cooling effect.

Chemical Structure

Levomenthol
CAS#2216-51-5

Theoretical Analysis

MedKoo Cat#: 596450

Name: Levomenthol

CAS#: 2216-51-5

Chemical Formula: C10H20O

Exact Mass: 156.1514

Molecular Weight: 156.27

Elemental Analysis: C, 76.86; H, 12.90; O, 10.24

Price and Availability

Size Price Availability Quantity
25g USD 250.00 2 Weeks
100g USD 450.00 2 Weeks
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Related CAS #
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Synonym
Levomenthol; D-(-)-Menthol; l-Menthol; Levomentholum; NSC 62788; NSC62788; NSC-62788; FEMA No. 2665; U.S.P. Menthol;
IUPAC/Chemical Name
(1R)-2-isopropyl-5-methylcyclohexan-1-ol
InChi Key
NOOLISFMXDJSKH-UDNWOFFPSA-N
InChi Code
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
SMILES Code
O[C@H]1C(C(C)C)CCC(C)C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
(-)-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.
In vitro activity:
It was shown that (-)-Menthol inhibited the proliferation of the cells in a dose- and time-dependent manner, inhibited topoisomerase I, IIa and IIbeta, but promoted the levels of NF-kappaB gene expression based on the Western blot and polymerase chain reaction (PCR) and cDNA microarray methods. Reference: Anticancer Res. 2005 May-Jun;25(3B):2069-74. https://pubmed.ncbi.nlm.nih.gov/16158947/
In vivo activity:
The effects of (-)-menthol on WEHI-3 cells in vivo (BALBIc mice) were also examined, and it was observed that the Mac-3 and CD11b markers were decreased, indicating inhibition of differentiation of the precursor of macrophage and granulocyte. The weights of liver and spleen samples from mice treated with (-)-menthol were found to be decreased compared to untreated animals. Reference: In Vivo. 2007 Mar-Apr;21(2):285-9. https://pubmed.ncbi.nlm.nih.gov/17436578/
Solvent mg/mL mM comments
Solubility
Ethanol 30.0 191.98
Ethanol:PBS (pH 7.2) (1:2) 0.3 2.11
Water 1.9 12.09
DMF 30.0 191.98
DMSO 55.0 351.96
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 156.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Suzuki N, Tsugami Y, Wakasa H, Suzuki T, Nishimura T, Kobayashi K. Menthol from Mentha piperita Suppresses the Milk Production of Lactating Mammary Epithelial Cells In Vivo and In Vitro. Mol Nutr Food Res. 2020 Nov 14:e2000853. doi: 10.1002/mnfr.202000853. Epub ahead of print. PMID: 33188562. 2. Lin JP, Lu HF, Lee JH, Lin JG, Hsia TC, Wu LT, Chung JG. (-)-Menthol inhibits DNA topoisomerases I, II alpha and beta and promotes NF-kappaB expression in human gastric cancer SNU-5 cells. Anticancer Res. 2005 May-Jun;25(3B):2069-74. PMID: 16158947. 3. Lu HF, Liu JY, Hsueh SC, Yang YY, Yang JS, Tan TW, Kok LF, Lu CC, Lan SH, Wu SY, Liao SS, Ip SW, Chung JG. (-)-Menthol inhibits WEHI-3 leukemia cells in vitro and in vivo. In Vivo. 2007 Mar-Apr;21(2):285-9. PMID: 17436578. 4. Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C. Menthol: a natural analgesic compound. Neurosci Lett. 2002 Apr 12;322(3):145-8. doi: 10.1016/s0304-3940(01)02527-7. PMID: 11897159.
In vitro protocol:
1. Suzuki N, Tsugami Y, Wakasa H, Suzuki T, Nishimura T, Kobayashi K. Menthol from Mentha piperita Suppresses the Milk Production of Lactating Mammary Epithelial Cells In Vivo and In Vitro. Mol Nutr Food Res. 2020 Nov 14:e2000853. doi: 10.1002/mnfr.202000853. Epub ahead of print. PMID: 33188562. 2. Lin JP, Lu HF, Lee JH, Lin JG, Hsia TC, Wu LT, Chung JG. (-)-Menthol inhibits DNA topoisomerases I, II alpha and beta and promotes NF-kappaB expression in human gastric cancer SNU-5 cells. Anticancer Res. 2005 May-Jun;25(3B):2069-74. PMID: 16158947.
In vivo protocol:
1. Lu HF, Liu JY, Hsueh SC, Yang YY, Yang JS, Tan TW, Kok LF, Lu CC, Lan SH, Wu SY, Liao SS, Ip SW, Chung JG. (-)-Menthol inhibits WEHI-3 leukemia cells in vitro and in vivo. In Vivo. 2007 Mar-Apr;21(2):285-9. PMID: 17436578. 2. Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C. Menthol: a natural analgesic compound. Neurosci Lett. 2002 Apr 12;322(3):145-8. doi: 10.1016/s0304-3940(01)02527-7. PMID: 11897159.
1: Karami N, Karimi A, Aliahmadi A, Mirzajan F, Rezadoost H, Ghassempour A, Fallah F. Identification of bacteria using volatile organic compounds. Cell Mol Biol (Noisy-le-grand). 2017 Feb 28;63(2):112-121. doi: 10.14715/cmb/2017.63.2.18. PubMed PMID: 28364792. 2: Birring SS, Brew J, Kilbourn A, Edwards V, Wilson R, Morice AH. Rococo study: a real-world evaluation of an over-the-counter medicine in acute cough (a multicentre, randomised, controlled study). BMJ Open. 2017 Jan 16;7(1):e014112. doi: 10.1136/bmjopen-2016-014112. PubMed PMID: 28093442; PubMed Central PMCID: PMC5253529. 3: Wallengren J. Tea tree oil attenuates experimental contact dermatitis. Arch Dermatol Res. 2011 Jul;303(5):333-8. doi: 10.1007/s00403-010-1083-y. Epub 2010 Sep 24. PubMed PMID: 20865268.