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P45680

Sigma-Aldrich

(+)-α-Pinene

98%

Synonym(s):

(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, (1R,5R)-2-Pinene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
7785-70-8
Molecular Weight:
136.23
Beilstein:
2038653
EC Number:
232-087-8
MDL number:
MFCD00001346
UNSPSC Code:
12352002
PubChem Substance ID:
24898553
NACRES:
NA.22

Assay

98%

optical activity

[α]/D 35 to 54, neat

optical purity

ee: ≥85% (GLC)

autoignition temp.

491 °F

refractive index

n20/D 1.465 (lit.)

bp

155-156 °C (lit.)

mp

−62 °C (lit.)

density

0.858 g/mL at 20 °C (lit.)

SMILES string

CC1=CC[C@@H]2C[C@H]1C2(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-/m1/s1

InChI key

GRWFGVWFFZKLTI-RKDXNWHRSA-N

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General description

(+)-α-Pinene, a monoterpene, is a bio-jet fuel precursor. It undergoes ozonolysis to produce secondary organic aerosol (SOA) mass.

Application

(+)-α-Pinene can be used:
  • To prepare chiral organoboranes, which are used in the synthesis of optically active compounds and in Suzuki coupling.
  • In the synthesis of chiral pyridine-type N-oxides as catalysts for the allylation of aromatic aldehydes.
  • To synthesize 2,3-pinane diamine, a chiral auxiliary in several catalysts and reagents.

(+)-α-Pinene has been used in a tolerance testing procedure to detect the genes in Marinobacter aquaeolei, for engineering a pinene tolerant Escherichia coli.

Signal Word

Danger

Hazard Statements

H226,H304,H315,H317,H410

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °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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New pyridine-derived N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes.
Malkov A V, et al.
J. Mol. Catal. A: Chem., 196(1-2), 179-186 (2003)
Chiral synthesis via organoboranes. 18. Selective reductions. 43. Diisopinocampheylchloroborane as an excellent chiral reducing reagent for the synthesis of halo alcohols of high enantiomeric purity. A highly enantioselective synthesis of both optical isomers of Tomoxetine, Fluoxetine, and Nisoxetine.
Srebnik M, et al.
The Journal of Organic Chemistry, 53(13), 2916-2920 (1988)
Synthesis and characterization of novel chiral 1, 2-diamines derived from α-pinene.
Suzuki T, et al.
Chemistry Letters (Jpn), 34(11), 1476-1477 (2005)
Coating of soot and (NH4)2SO4 particles by ozonolysis products of a-pinene.
Saathoff, H., et al.
Journal of Aerosol Science, 34(10), 1297-1321 (2003)
Timothy A Tomko et al.
Biotechnology for biofuels, 8, 165-165 (2015-10-09)
Recent metabolic engineering efforts have generated microorganisms that can produce biofuels, including bio-jet fuels, however these fuels are often toxic to cells, limiting production yields. There are natural examples of microorganisms that have evolved mechanisms for tolerating hydrocarbon-rich environments, such
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