(S)-(−)-Citronellal

Name: (<I>S</I>)-(−)-Citronellal
Brand: ALDRICH

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

Assay:

96%

Form:

liquid

Key Documents

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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

Chemical Building Blocks

Aldehydes

Catalysts

Chiral Catalysts & Ligands

Organic Building Blocks

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This Item	303488	C83201	364428
Sigma-Aldrich 373753 (S)-(−)-Citronellal	Sigma-Aldrich 303488 (S)-(−)-β-Citronellol	Sigma-Aldrich C83201 β-Citronellol	Sigma-Aldrich 364428 (S)-(−)-Citronellic acid
assay 96%	assay ≥97%	assay 95%	assay 98%
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
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.)
form liquid	form liquid	form liquid	form liquid
optical activity [α]20/D −15°, neat	optical activity [α]20/D −4.5°, neat	optical activity -	optical activity [α]25/D −8°, neat

Application

(S)-(-)-Citronellal may be used in the synthesis of bioactive compounds like (+)-hexahydrocannabinol[1], (S)-isopulegol[2], machaeriols A and B.[3]

General description

(S)-(-)-Citronellal is a monoterpenoid compound mainly found in Corymbia citriodora and Cymbopogon nardus essential oils.[4]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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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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)

Engineering the Enantioselectivity of Yeast Old Yellow Enzyme OYE2y in Asymmetric Reduction of (E/Z)-Citral to (R)-Citronellal.

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

One-step microwave-assisted asymmetric cyclisation/hydrogenation of citronellal to menthols using supported nanoparticles on mesoporous materials.

Alina Mariana Balu et al.

Organic & biomolecular chemistry, 8(12), 2845-2849 (2010-05-01)

The selective conversion of citronellal to menthols, with good diastereoselectivities to (-)-menthol for the case of (+)-citronellal as starting material, can effectively be carried out in a one-step reaction under microwave irradiation catalysed by supported nanoparticles on mesoporous materials. 2%

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