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W266523

Sigma-Aldrich

L-Menthol

greener alternative

natural, ≥99%, FCC, FG

Synonym(s):

(1R,2S,5R)-(−)-Menthol, (−)-Menthol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
2216-51-5
Molecular Weight:
156.27
FEMA Number:
2665
Beilstein:
1902293
EC Number:
218-690-9
Council of Europe no.:
65c
MDL number:
MFCD00062979
UNSPSC Code:
12164502
PubChem Substance ID:
24901227
Flavis number:
2.218
NACRES:
NA.21
grade:
FG
Halal
Kosher
natural
food allergen:
no known allergens
Pricing and availability is not currently available.

grade

FG
Halal
Kosher
natural

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 117

vapor pressure

0.8 mmHg ( 20 °C)

Assay

≥99%

optical activity

[α]20/D −49°, c = 10 in 95% ethanol

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

bp

212 °C (lit.)

mp

41-45 °C (lit.)

density

0.89 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

greener alternative category

Aligned

Organoleptic

minty; cooling; peppermint

SMILES string

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

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

InChI key

NOOLISFMXDJSKH-KXUCPTDWSA-N

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General description

L-Menthol is the principal component of peppermint oil. It is widely used in confectionaries cosmetics and toothpaste for its characteristic peppermint flavor and cooling effect.[1]

Application

L-Menthol can be used as a model flavor compound to prepare flavor encapsulated porous cellulose particles for food processing applications.[2]

Biochem/physiol Actions

Taste at 25 ppm

Other Notes

Natural occurrence: Mentha species.

Disclaimer

The substance W266523 has no REACH registration because the only supported use is the use in medicinal products for human or veterinary use or in food or feedingstuffs according to article 2 of the REACH Regulation (EC) No 1907/2006.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR4802
SHBR1676
SHBQ5271
SHBR0412
SHBQ5270

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SAFC

1.05995

(-)-Menthol

Menthol European Pharmacopoeia (EP) Reference Standard

M0350000

Menthol

(−)-Menthol analytical standard

Supelco

63660

(−)-Menthol

Menthol United States Pharmacopeia (USP) Reference Standard

USP

1381709

Menthol

Levomenthol British Pharmacopoeia (BP) Reference Standard

BP772

Levomenthol

L-Menthone mixture of isomers, ≥96%, FCC, FG

Sigma-Aldrich

W266701

L-Menthone

An investigation of flavor encapsulation comprising of regenerated cellulose as core and carboxymethyl cellulose as wall
Ma M, et al.
Iranian Polymer Journal, 22(9), 689-695 (2013)
Optimized synthesis of lipase-catalyzed l-menthyl butyrate by Candia rugosa lipase.
Shih L, et al.
Food Chemistry, 100(3), 1223-1228 (2007)
Thomas Voets et al.
Nature chemical biology, 3(3), 174-182 (2007-02-13)
TRPM8, a member of the transient receptor potential (TRP) channel superfamily, is expressed in thermosensitive neurons, in which it functions as a cold and menthol sensor. TRPM8 and most other temperature-sensitive TRP channels (thermoTRPs) are voltage gated; temperature and ligands
H G Grigoleit et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 12(8), 612-616 (2005-08-27)
The principal pharmacodynamic effect of peppermint oil relevant to the gastrointestinal tract is a dose-related antispasmodic effect on the smooth musculature due to the interference of menthol with the movement of calcium across the cell membrane. The choleretic and antifoaming
Robert J Stein et al.
The Journal of urology, 172(3), 1175-1178 (2004-08-18)
Overactive bladder symptoms due to various etiologies have been successfully treated with capsaicin by desensitization of the temperature sensitive vanilloid receptor TRPV1. Recently another temperature sensitive receptor, TRPM8, activated by menthol and cool temperatures (8C to 28C) was described that
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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. What does SAMPLE-K mean?

    1 answer

    1. The Sample-K SKU designation refers to a sample amount of the item. This smaller quantity is often utilized to qualify the material for use without purchasing the larger quantities listed - in this case the 1KG and the 4KG.

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