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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
Empirical Formula (Hill Notation):
C10H16
CAS Number:
Molecular Weight:
136.23
Beilstein:
1903790
EC Number:
MDL number:
eCl@ss:
39011007
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.7 (vs air)

Quality Level

vapor pressure

~3 mmHg ( 20 °C)

assay

≥97.0% (GC)
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.

Packaging

25, 100 g in glass bottle

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

88.3 °F

Flash Point(C)

31.3 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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