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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

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)(OH)CH=CH2
CAS Number:
Molecular Weight:
154.25
Beilstein/REAXYS Number:
1721487
EC Number:
MDL number:
UNSPSC Code:
12352002
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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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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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)
Total Synthesis of (-)-5, 6-Dihydrocineromycin B
Li, Guozhi, et al.
The Journal of Organic Chemistry, 74(3), 1356-1359 (2009)
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
Carolina E Reisenman et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 24(11), 2602-2611 (2004-03-19)
Projection neurons (PNs) with arborizations in the sexually dimorphic "lateral large female glomerulus" (latLFG) in the antennal lobe (AL) of the moth Manduca sexta previously were shown to respond preferentially to antennal stimulation with (+/-)linalool, a volatile compound commonly emitted
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

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