439061
(−)-Isopulegol
99%
Synonym(s):
(1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol, (1R,3R,4S)-p-Menth-8-en-3-ol
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About This Item
Empirical Formula (Hill Notation):
C10H18O
CAS Number:
Molecular Weight:
154.25
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-940-6
Beilstein/REAXYS Number:
1906573
MDL number:
Assay:
99%
Form:
liquid
Quality Level
assay
99%
form
liquid
optical activity
[α]20/D −22°, neat
refractive index
n20/D 1.471 (lit.)
bp
212 °C (lit.)
density
0.912 g/mL at 25 °C (lit.)
functional group
hydroxyl
SMILES string
C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
InChI
1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
InChI key
ZYTMANIQRDEHIO-KXUCPTDWSA-N
General description
Isopulegol is monoterpene alcohol, a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste.
Application
(−)-Isopulegol can be used as a starting material for the enantioselective preparation of:
- 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,·
- Stereoisomers of 5,9-dimethylpentadecane.
- Octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst.
- p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
172.4 °F - closed cup
flash_point_c
78 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol over acid modified montmorillonite clays: Effect of acidity on the Prins cyclization
Timofeeva MN, et al.
J. Mol. Catal. A: Chem., 398, 26-34 (2015)
Green synthesis of (-)-isopulegol from (+)-citronellal: application to essential oil of citronella
Jacob RG, et al.
Tetrahedron Letters, 44(18), 3605-3608 (2003)
Synthesis and Absolute Configuration at C (8) of `p-Menthane-3, 8, 9-triol?Derived from (-)-Isopulegol
Yuasa Y and Yuasa Y
Helvetica Chimica Acta, 87(10), 2602-2607 (2004)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 439061-1ML | 04061832245911 |