Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

373753

Sigma-Aldrich

(S)-(−)-Citronellal

96%

Synonym(s):

(−)-Citronellal, (3S)-3,7-Dimethyl-6-octenal

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CHO
CAS Number:
5949-05-3
Molecular Weight:
154.25
Beilstein:
1720790
EC Number:
227-707-9
MDL number:
MFCD00075588
UNSPSC Code:
12352114
PubChem Substance ID:
24863258
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

96%

form

liquid

optical activity

[α]20/D −15°, neat

refractive index

n20/D 1.446 (lit.)

density

0.851 g/mL at 25 °C (lit.)

functional group

aldehyde

SMILES string

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

InChI

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

InChI key

NEHNMFOYXAPHSD-JTQLQIEISA-N

Related Categories

General description

(S)-(-)-Citronellal is a monoterpenoid compound mainly found in Corymbia citriodora and Cymbopogon nardus essential oils.[1]

Application

(S)-(-)-Citronellal may be used in the synthesis of bioactive compounds like (+)-hexahydrocannabinol[2], (S)-isopulegol[3], machaeriols A and B.[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCC5284
BCBJ9098V
BCBF6853V
1446281V
1446280

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

First synthesis of antimalarial Machaeriols A and B.
Chittiboyina AG, et al.
Tetrahedron Letters, 45(8), 1689-1691 (2004)
Asymmetric cyclization of unsaturated aldehydes catalyzed by a chiral Lewis acid.
Sakane S, et al.
Tetrahedron Letters, 26(45), 5535-5538 (1985)
Efficient one-pot synthetic approaches for cannabinoid analogues and their application to biologically interesting (-)-hexahydrocannabinol and (+)-hexahydrocannabinol.
Lee YR and Xia L.
Tetrahedron Letters, 49(20), 3283-3287 (2008)
Xiangxian Ying et al.
Molecules (Basel, Switzerland), 24(6) (2019-03-21)
The members of the Old Yellow Enzyme (OYE) family are capable of catalyzing the asymmetric reduction of (E/Z)-citral to (R)-citronellal-a key intermediate in the synthesis of L-menthol. The applications of OYE-mediated biotransformation are usually hampered by its insufficient enantioselectivity and
M S Melo et al.
Pharmaceutical biology, 48(4), 411-416 (2010-07-22)
Citronellal is a monoterpene reported to be a major component of the essential oils in various aromatic species of plants. The present study evaluated the central nervous system depressant and antinociceptive properties of citronellal through behavioral experimental models. Following intraperitoneal
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service