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Merck

373753

(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
UNSPSC Code:
12352114
NACRES:
NA.22
PubChem Substance ID:
24863258
EC Number:
227-707-9
Beilstein/REAXYS Number:
1720790
MDL number:
MFCD00075588

Key Documents

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Product Name

(S)-(−)-Citronellal, 96%

InChI key

NEHNMFOYXAPHSD-JTQLQIEISA-N

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

SMILES string

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

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

Quality Level

100

Related Categories

Application

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

General description

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

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

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC5284
BCBJ9098V
BCBF6853V
1446281V
1446280

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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
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
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