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112089

Sigma-Aldrich

(−)-β-Pinene

99%

Synonym(s):

(-)-beta-Pinene, (1S)-(−)-β-Pinene, (1S,5S)-2(10)-Pinene, (1S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
18172-67-3
Molecular Weight:
136.23
Beilstein:
2038282
EC Number:
242-060-2
MDL number:
MFCD00001345
UNSPSC Code:
12352212
eCl@ss:
39011007
PubChem Substance ID:
24847064
NACRES:
NA.22

vapor density

4.7 (vs air)

vapor pressure

~2 mmHg ( 20 °C)

Assay

99%

optical activity

[α]20/D −21°, neat

refractive index

n20/D 1.478 (lit.)

bp

165-167 °C (lit.)

mp

−61 °C (lit.)

density

0.859 g/mL at 25 °C

SMILES string

[H][C@]12CCC(=C)[C@]([H])(C1)C2(C)C

InChI

1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1

InChI key

WTARULDDTDQWMU-IUCAKERBSA-N

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General description

(-)-β-Pinene belongs to the terpenes family and is used as a starting material or intermediate in organic synthesis.

Application

(-)-β-Pinene has been used as test compound to assess its fumigant toxicity against all life stages of confused flour beetle and Mediterranean flour moth, via single-dose test. It has been used as a standard during the determination of constituents of the essential oil of Achillea ligustica by gas chromatography-mass spectrometry. (-)-β-Pinene can be used as a starting material to synthesize (1R,2S,3R,5R)-3-amino-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane and (+)-nopinone.

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)

102.2 °F - closed cup

Flash Point(C)

39 °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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Chiral terpene auxiliaries. Part 1: Highly enantioselective reduction of ketones with borane catalyzed by an oxazaborolidine derived from (-)-?-pinene
Krzeminski MP and Wojtczak A
Tetrahedron Letters, 46(48), 8299-8302 (2005)
Fumigant toxicity of monoterpenoid compounds against the confused flour beetle, Tribolium confusum Jacquelin du Val.(Coleoptera: Tenebrionidae).
Saglam O and Ozder N.
Turkiye Entomoloji Dergisi (Turkish Journal of Entomology), 37(4) (2013)
Synthesis of (+)-Methyl Phaseate and Its Isomer from (-)-?-Pinene
Takahashi S, et al.
Agricultural and Biological Chemistry, 53(10), 2711-2718 (1989)
Dual stereoselectivity in the dialkylzinc reaction using (-)-?-pinene derived amino alcohol chiral auxiliaries
Binder CM, et al
The Journal of Organic Chemistry, 74(6), 2337-2343 (2009)
Jean-Jacques Filippi et al.
Journal of agricultural and food chemistry, 54(17), 6308-6313 (2006-08-17)
The essential oil of Achillea ligustica from Corsica was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 82 compounds representing 94.0% of the oil were tentatively identified. The main constituents were the camphane derivatives, representing
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