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373753

Sigma-Aldrich

(S)-(−)-Citronellal

96%

Synonym(s):

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

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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

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.)

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.

Application

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

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

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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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
Osnat Altshuler et al.
Journal of natural products, 76(9), 1598-1604 (2013-08-21)
Citronellal is a major component of Corymbia citriodora and Cymbopogon nardus essential oils. Herein it is shown that whereas (+)-citronellal (1) is an effective microtubule (MT)-disrupting compound, (-)-citronellal (2) is not. Quantitative image analysis of fibroblast cells treated with 1
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