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224464

Sigma-Aldrich

(1S,2R,5S)-(+)-Menthol

99%

Synonym(s):

(+)-Menthol, (1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
15356-60-2
Molecular Weight:
156.27
Beilstein:
1902292
EC Number:
239-387-8
MDL number:
MFCD00062983
UNSPSC Code:
12352212
PubChem Substance ID:
24853440
NACRES:
NA.22

vapor pressure

0.8 mmHg ( 20 °C)

Quality Level

100

Assay

99%

form

solid

optical activity

[α]23/D +48°, c = 10 in ethanol

optical purity

ee: 96% (GLC)

bp

103-104 °C/9 mmHg (lit.)

mp

43-44 °C (lit.)

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-/m0/s1

InChI key

NOOLISFMXDJSKH-AEJSXWLSSA-N

Gene Information

human ... UGT1A4(54657)

Related Categories

General description

(1S,2R,5S)-(+)-menthol is a chiral secondary alcohol. Its alcohol group can be protected as 2-tetrahydrofuranyl ether by reacting with bromotrichloromethane and tetrahydrofuran.

Application

(1S,2R,5S)-(+)-menthol can undergo acylation with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate to form the corresponding acylated products.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate.
Procopiou PA, et al.
The Journal of Organic Chemistry, 63(7), 2342-2347 (1998)
An efficient and extremely mild method for protecting alcohols as 2-tetrahydrofuranyl ethers.
Barks JM, et al.
Tetrahedron Letters, 41(32), 6249-6252 (2000)

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