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62139

Sigma-Aldrich

(−)-Linalool

≥95.0% (sum of enantiomers, GC)

Synonym(s):
(R)-(−)-3,7-Dimethyl-1,6-octadien-3-ol
Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)(OH)CH=CH2
CAS Number:
Molecular Weight:
154.25
Beilstein:
1721487
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95.0% (sum of enantiomers, GC)

optical activity

[α]20/D −18±3°, neat

refractive index

n20/D 1.4615 (lit.)
n20/D 1.462

bp

198 °C (lit.)

density

0.862 g/mL at 20 °C (lit.)

SMILES string

C\C(C)=C\CC[C@@](C)(O)C=C

InChI

1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m0/s1

InChI key

CDOSHBSSFJOMGT-JTQLQIEISA-N

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General description

(-)-Linalool is a monoterpene compound mainly found in many essential oils. It shows anti-nociceptive and anti-inflammatory activity.

Application

(-)-Linalool can be used as a reactant in:
  • The enantioselective preparation of ophiobolin sesterterpene via diastereoselective reductive radical cascade cyclization.
  • The total synthesis of (-)-5,6-dihydrocineromycin B via (-)-linalool O-triethylsilyl ether.;
  • The total synthesis of pladienolide B analog.

Packaging

25, 100 mL in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 62139.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

166.3 °F - closed cup

Flash Point(C)

74.6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Synthesis of a pladienolide B analogue with the fully functionalized core structure
Mu?ller S, et al.
Organic Letters, 13(15), 3940-3943 (2011)
(-)-Linalool produces antinociception in two experimental models of pain.
Peana AT, et al.
European Journal of Pharmacology, 460(1), 37-41 (2003)
Amy L Parachnowitsch et al.
Plant signaling & behavior, 8(1), e22704-e22704 (2012-12-12)
Natural selection is thought to have shaped the evolution of floral scent; however, unlike other floral characters, we have a rudimentary knowledge of how phenotypic selection acts on scent. We found that floral scent was under stronger selection than corolla
Nan Zhang et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 23(14), 1727-1734 (2016-12-04)
Essential oil from Cananga odorata (ylang-ylang essential oil, YYO) is usually used in reducing blood pressure, improving cognitive functioning in aromatherapy in human. Few reports showed its effect on anxiety behaviors. To investigate the anxiolytic effects of YYO exposure on
Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade
Brill ZG, et al.
Science (New York, N.Y.), 352(6289), 1078-1082 (2016)

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