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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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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)
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)
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
Kazumi Osada et al.
Bioscience, biotechnology, and biochemistry, 76(9), 1781-1784 (2012-09-14)
To determine whether ingestion of citronellal decreases the attractive power of the male mouse urinary odor, female mice were used in preference tests. A series of tests revealed that the female mice preferred voided urine odors from aged mice over
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