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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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25 ML
$70.70
100 ML
$166.00

About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)(OH)CH=CH2
CAS Number:
126-91-0
Molecular Weight:
154.25
Beilstein/REAXYS Number:
1721487
EC Number:
204-811-2
MDL number:
MFCD00135469
UNSPSC Code:
12352002
PubChem Substance ID:
57651876
NACRES:
NA.22

$70.70

Available to ship onApril 29, 2025Details

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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

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General description

(-)-Linalool is a monoterpene compound mainly found in many essential oils.[1][2] It shows anti-nociceptive[1] and anti-inflammatory activity.[2]

Application

(-)-Linalool can be used as a reactant in:
  • The enantioselective preparation of ophiobolin sesterterpene via diastereoselective reductive radical cascade cyclization.[3]
  • The total synthesis of (-)-5,6-dihydrocineromycin B via (-)-linalool O-triethylsilyl ether.[4];
  • The total synthesis of pladienolide B analog.[5]

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_germany

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)
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
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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