Skip to Content
Merck
CN
All Photos(1)

Key Documents

View All Documentation

62638

Sigma-Aldrich

(+)-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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

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

SMILES string

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

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

InChI key

HICYDYJTCDBHMZ-UKTARXLSSA-N

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

197.6 °F - closed cup

Flash Point(C)

92 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCC4418

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Regioselective oxidation of (+)-α -longipinene by Aspergillus niger
Sakata K and Miyazawa M
Journal of Oleo Science, 59(5), 261-265 (2010)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service