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80613

Sigma-Aldrich

(−)-trans-Pinocarveol

≥96.0% (sum of enantiomers, GC)

Synonym(s):

(1S,3R,5S)-2(10)-Pinen-3-ol, (1S,3R,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
547-61-5
Molecular Weight:
152.23
Beilstein/REAXYS Number:
5730571
EC Number:
208-927-4
MDL number:
MFCD00210086
UNSPSC Code:
12352002
PubChem Substance ID:
57652835
NACRES:
NA.22

assay

≥96.0% (sum of enantiomers, GC)

form

liquid

optical activity

[α]20/D −72±3°, neat

color

opaque white

refractive index

n20/D 1.500

density

0.979 g/mL at 20 °C (lit.)

SMILES string

CC1(C)[C@@H]2C[C@@H](O)C(=C)[C@H]1C2

InChI

1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m0/s1

InChI key

LCYXQUJDODZYIJ-DJLDLDEBSA-N

General description

(-)-trans-Pinocarveol is an allyl alcohol. It is formed during the allylic oxidation of β-pinene using hydrogen peroxide-selenium dioxide or from the isomerization of α-pinene oxide over zirconium oxide.

Other Notes

Volatile component of essential oils occurring in many plants. Starting material for highly pure (-)-nopinone

Storage Class

12 - Non Combustible Liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
334956/1

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Allylic Oxidation with Hydrogen Peroxide-Selenium Dioxide: trans-Pinocarveol.
Coxon JM, et al.
Organic Syntheses, 25-25 (1977)
Isomerization of a-pinene oxide over solid acids and bases.
Arata K and Tanabe K.
Chemistry Letters (Jpn), 8(8), 1017-1018 (1979)
P. Lavalee et al.
The Journal of Organic Chemistry, 51, 1362-1362 (1986)

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