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62139

(−)-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:
126-91-0
Molecular Weight:
154.25
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
57651876
EC Number:
204-811-2
Beilstein/REAXYS Number:
1721487
MDL number:
MFCD00135469
Assay:
≥95.0% (sum of enantiomers, GC)
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Quality Level

100

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.)

functional group

hydroxyl

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

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.

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

166.3 °F - closed cup

flash_point_c

74.6 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0287
BCCJ0902
BCCF5206
BCBV9483
BCBX7222

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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)
Synthesis of a pladienolide B analogue with the fully functionalized core structure
Mu?ller S, et al.
Organic Letters, 13(15), 3940-3943 (2011)
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