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Merck
CN

62638

(+)-α-Longipinene

≥97.0% (sum of enantiomers, GC)

Synonym(s):

(1R,2S,7R,8R)-2,6,6,9-Tetramethyltricyclo[5.4.0.02.8]undec-9-ene

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About This Item

Empirical Formula (Hill Notation):
C15H24
CAS Number:
5989-08-2
Molecular Weight:
204.35
NACRES:
NA.22
PubChem Substance ID:
57651909
UNSPSC Code:
12352002
MDL number:
MFCD00077624

Key Documents

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Product Name

(+)-α-Longipinene, ≥97.0% (sum of enantiomers, GC)

InChI

1S/C15H24/c1-10-6-7-11-13-12(10)15(11,4)9-5-8-14(13,2)3/h6,11-13H,5,7-9H2,1-4H3/t11-,12+,13+,15-/m1/s1

SMILES string

[H][C@@]12CC=C(C)[C@@]3([H])[C@@]1([H])C(C)(C)CCC[C@]23C

InChI key

HICYDYJTCDBHMZ-UKTARXLSSA-N

assay

≥97.0% (sum of enantiomers, GC)

form

liquid

optical activity

[α]20/D +25±1°, neat

refractive index

n20/D 1.493

bp

244-246 °C (lit.)

density

0.915 g/mL at 20 °C (lit.)

storage temp.

2-8°C

Application

(+)-α-Longipinene can be used as a starting material for the synthesis of new terpenoids, (+)-(5S)-5,12-dihydroxy-α-longipinene, (-)-(5R)-5,12-dihydroxy-α-longipinene, and (+)-12-hydroxy-α-longipinen-5-one by oxidation reaction using Aspergillus niger as a biocatalyst. It can be oxidized using lead tetraacetate into tertiary alcohol, longi-cis-verbenol, longi-trans-verbenol, longi-cis-β-crysanthenol, longiverbenone, longi-trans- β -crysanthenol, 2 β,3 β -dihydroxylongipinane, 4 α,8-dihydroxy- α -Iongipinene, and 4 β,8-dihydroxy- α -longipinene.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

197.6 °F - closed cup

flash_point_c

92 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC4418

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Regioselective oxidation of (+)-α -longipinene by Aspergillus niger
Sakata K and Miyazawa M
Journal of Oleo Science, 59(5), 261-265 (2010)
Novel sesquiterpene alcohol prepared from the oxidation of α -longipinene with lead tetraacetate
Iwamuro H, et al.
Agricultural and Biological Chemistry, 47(7), 1637-1638 (1983)
Ramona Makarow et al.
Scientific reports, 10(1), 5194-5194 (2020-04-07)
Explorative experiments were done to figure out differences in the emission of volatile organic compounds (VOCs) of not infested trees and trees infested by Anoplophora glabripennis (Asian longhorn beetle, ALB), a quarantine pest. Therefore, VOCs from some native insect species

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