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402753

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:
Molecular Weight:
136.23
Beilstein/REAXYS Number:
2038282
EC Number:
MDL number:
UNSPSC Code:
12352212
eCl@ss:
39011007
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.7 (vs air)

Quality Level

vapor pressure

~2 mmHg ( 20 °C)

assay

≥99%

form

liquid

optical activity

[α]25/D −22°, neat

optical purity

ee: 97% (GLC)

refractive index

n20/D 1.478 (lit.)

bp

165-167 °C (lit.)

mp

−61 °C (lit.)

density

0.866 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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Application

(-)-β-Pinene has been used as a standard for the analysis of terpenoid compounds in plant essential oils by GC analysis. It may be used as a building block to synthesize natural products such as grandisol, robustadial and (+)-nopinone. (-)-β-Pinene undergoes hydroformylation in the presence of platinum/tin catalysts to form trans-10-formylpinane.

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

102.2 °F - closed cup

flash_point_c

39 °C - closed cup

ppe

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


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Tetrahedron Letters, 30, 6653-6653 (1989)
Reduction of Legionella spp. in water and in soil by a citrus plant extract vapor.
Laird K, et al.
Applied and Environmental Microbiology, 80(19), 6031-6036 (2014)
Adalberto Alves Pereira Filho et al.
Frontiers in plant science, 12, 685864-685864 (2021-06-22)
The continuous and indiscriminate use of insecticides has been responsible for the emergence of insecticide resistant vector insect populations, especially in Aedes aegypti. Thus, it is urgent to find natural insecticide compounds with novel mode of action for vector control.
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)
Katie Laird et al.
Applied and environmental microbiology, 80(19), 6031-6036 (2014-07-27)
Legionnaires' disease is a severe form of pneumonia caused by Legionella spp., organisms often isolated from environmental sources, including soil and water. Legionella spp. are capable of replicating intracellularly within free-living protozoa, and once this has occurred, Legionella is particularly

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