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303461

Sigma-Aldrich

(R)-(+)-β-Citronellol

95%

Synonym(s):

(+)-β-Citronellol, (R)-3,7-Dimethyl-6-octen-1-ol

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CH2OH
CAS Number:
1117-61-9
Molecular Weight:
156.27
Beilstein/REAXYS Number:
1721506
EC Number:
214-250-5
MDL number:
MFCD00063215
UNSPSC Code:
12352002
PubChem Substance ID:
24858125
NACRES:
NA.22

vapor pressure

~0.02 mmHg ( 25 °C)

Quality Level

100

assay

95%

form

liquid

optical activity

[α]19/D +5.3°, neat

refractive index

n20/D 1.456 (lit.)

bp

112-113 °C/12 mmHg (lit.)

density

0.857 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](CCO)CC\C=C(\C)C

InChI

1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1

InChI key

QMVPMAAFGQKVCJ-SNVBAGLBSA-N

Related Categories

Application

(R)-(+)-β-Citronellol can be used to prepare:
  • (R)-(+)-β-citronellyl acetate by treating with vinyl acetate via trans esterification reaction using immobilized Rhizomucor miehei lipase as biocatalyst.
  • (R)-(+)-citronellal and (R)-(+)-citronellic acid by the oxidation reaction.
  • Citronellol aziridine by treating with 2,2,2-trichloroethoxysulfonamide by intermolecular olefin aziridination.

It can also be used as a starting material for the synthesis of (+)-integerrinecic acid lactone.
(R)-(+)-β-Citronellol can undergo:
  • Oxidation to form (R)-(+)-citronellal, an antifungal agent and (R)-(+)-citronellic acid.
  • Intermolecular olefin aziridination with 2,2,2-trichloroethoxysulfonamide to form citronellol aziridine for ring-opening reactions.
  • Series of reactions to form α2δ-ligands for treating generalized anxiety disorder and insomnia.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

212.0 °F - closed cup

flash_point_c

100 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN5254
MKCN3270
MKCM2931
MKCM2935
MKCL2027

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Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids.
Yabuuchi T and Kusumi T
The Journal of Organic Chemistry, 65(2), 397-404 (2000)
Rh-catalyzed alkene oxidation: a highly efficient and selective process for preparing N-alkoxysulfonyl aziridines.
Guthikonda K, et al.
Tetrahedron, 62(49), 11331-11342 (2006)
A novel synthesis of (+)-integerrinecic acid lactone from R-(+) β-citronellol
White JD and Jayasinghe LR
Tetrahedron Letters, 29(18), 2139-2142 (1988)
Abir B Majumder et al.
Chemistry Central journal, 1, 10-10 (2007-09-21)
Use of enzymes in low water media is now widely used for synthesis and kinetic resolution of organic compounds. The frequently used enzyme form is the freeze-dried powders. It has been shown earlier that removal of water molecules from enzyme
A very mild and chemoselective oxidation of alcohols to carbonyl compounds.
De Luca L, et al.
Organic Letters, 3(19), 3041-3043 (2001)
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