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373753

Sigma-Aldrich

(S)-(−)-Citronellal

96%

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Synonym(s):
(−)-Citronellal, (3S)-3,7-Dimethyl-6-octenal
Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CHO
CAS Number:
Molecular Weight:
154.25
Beilstein:
1720790
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
303488C83201364428
(S)-(−)-Citronellal 96%

Sigma-Aldrich

373753

(S)-(−)-Citronellal

β-Citronellol 95%

Sigma-Aldrich

C83201

β-Citronellol

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.446 (lit.)

refractive index

n20/D 1.456 (lit.)

refractive index

n20/D 1.456 (lit.)

refractive index

n20/D 1.453 (lit.)

density

0.851 g/mL at 25 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

density

0.857 g/mL at 25 °C (lit.)

density

0.926 g/mL at 25 °C (lit.)

optical activity

[α]20/D −15°, neat

optical activity

[α]20/D −4.5°, neat

optical activity

-

optical activity

[α]25/D −8°, neat

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

Signal Word

Warning

Hazard Statements

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

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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)
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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
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The biosynthesis of cyclic monoterpenes (C(10)) generally requires the cyclization of an activated linear precursor (geranyldiphosphate) by specific terpene cyclases. Cyclic triterpenes (C(30)), on the other hand, originate from the linear precursor squalene by the action of squalene-hopene cyclases (SHCs)

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