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274399

Sigma-Aldrich

(−)-α-Pinene

99%, optical purity ee: ≥86% (GLC)

Synonym(s):

(-)-alpha-Pinene, (1S)-(−)-α-Pinene, (1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, (1S,5S)-2-Pinene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
7785-26-4
Molecular Weight:
136.23
Beilstein/REAXYS Number:
1903790
EC Number:
232-077-3
MDL number:
MFCD00064145
UNSPSC Code:
12352002
eCl@ss:
39011007
PubChem Substance ID:
24856583
NACRES:
NA.22

vapor density

4.7 (vs air)

vapor pressure

~3 mmHg ( 20 °C)

assay

99%

form

liquid

optical activity

[α]20/D −50.0 to −46.0°, neat

optical purity

ee: ≥86% (GLC)

autoignition temp.

491 °F

refractive index

n20/D 1.465 (lit.)

bp

155-156 °C (lit.)

mp

-64 °C (lit.)

density

0.855 g/mL at 25 °C

SMILES string

CC1=CCC2CC1C2(C)C

InChI

1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1

InChI key

GRWFGVWFFZKLTI-IUCAKERBSA-N

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General description

α-Pinene is a monoterpene used in industries like fragrance, pharmaceuticals, flavor, and cosmetics. It is a major component of pine oil and turpentine oil. Isomerization of α-pinene yields industrially important compounds like camphene, limonene, and p-cymene.

Application

(−)-α-Pinene can be used:
  • To prepare chiral γ-amino alcohols, which are used as catalysts for the preparation of chiral 1-aryl-1-propanols using aromatic aldehydes.
  • As a substrate in the study of its t-BuOOH mediated oxidation catalyzed by Co(II) complex.
  • As a starting material for the synthesis of polyfunctionalized cyclobutane derivatives.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 2 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

88.3 °F

flash_point_c

31.3 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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Isomerisation of alpha-pinene using modified montmorillonite clays
Yadav MK, et al.
J. Mol. Catal. A: Chem., 216(1), 51-59 (2004)
Isomerization of alpha-pinene over dealuminated ferrierite-type zeolites
Rachwalik R, et al.
J. Catal., 252(2), 161-170 (2007)
Co (II) catalysed oxidation of alpha-pinene by molecular oxygen: Part III
Lajunen MK
J. Mol. Catal. A: Chem., 169(1-2), 33-40 (2001)
Enantioselective addition of diethylzinc to aldehydes catalyzed by ?-amino alcohols derived from (+)-and (-)-a-pinene.
Szakonyi Z, et al.
Tetrahedron Asymmetry, 17(2), 199-204 (2006)
Divergent routes to chiral cyclobutane synthons from (−)-alpha-pinene and their use in the stereoselective synthesis of dehydro amino acids
Moglioni AG, et al.
The Journal of Organic Chemistry, 65(13), 3934-3940 (2000)

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