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343641

Sigma-Aldrich

(R)-(+)-Citronellal

technical grade

Synonym(s):

(+)-Citronellal, (3R)-3,7-Dimethyl-6-octenal

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CHO
CAS Number:
2385-77-5
Molecular Weight:
154.25
Beilstein:
1720791
EC Number:
219-194-5
MDL number:
MFCD00067089
UNSPSC Code:
12352114
PubChem Substance ID:
24861185
NACRES:
NA.22

grade

technical grade

form

liquid

refractive index

n20/D 1.448 (lit.)

bp

207 °C (lit.)

density

0.851 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1

InChI key

NEHNMFOYXAPHSD-SNVBAGLBSA-N

Related Categories

General description

(R)-(+)-Citronellal is a monoterpenoid aldehyde. It is a chiral organic compound used as a building block in organic synthesis to prepare various chiral compounds. It is also used as a chiral catalyst or ligand in asymmetric reactions.

Application

(R)-(+)-Citronellal can be used as a reactant to synthesize various compounds such as L-menthol, caparratriene, and chalcogen-containing nitrone derivatives.

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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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
Daniel P Iwaniuk et al.
Chemical communications (Cambridge, England), 48(91), 11226-11228 (2012-10-16)
A rationally designed stereodynamic ICD probe carrying two terminal amino functions for chemo- and enantioselective sensing of citronellal is introduced. The sensor shows strong Cotton effects upon diimine formation which can be used for accurate ee determination.
Kazumi Osada et al.
Chemical senses, 36(2), 137-147 (2010-10-20)
Body odors provide a rich source of sensory information for other animals. There is considerable evidence to suggest that short-term fluctuations in body odor can be caused by diet; however, few, if any, previous studies have demonstrated that specific compounds
Gabriele Siedenburg et al.
Applied microbiology and biotechnology, 97(4), 1571-1580 (2012-04-25)
Squalene-hopene cyclases (SHCs) are prokaryotic enzymes that catalyse the cyclisation of the linear precursor squalene to pentacyclic hopene. Recently, we discovered that a SHC cloned from Zymomonas mobilis (ZMO-1548 gene product) has the unique property to cyclise the monoterpenoid citronellal
Despina J Bougioukou et al.
Chemical communications (Cambridge, England), 46(45), 8558-8560 (2010-10-06)
Simple strategies for using alkene reductase enzymes to produce gram-scale quantities of both (R)- and (S)-citronellal have been developed. The methodology is easily accessible to non-specialist laboratories, allowing alkene reductases to be added to the toolbox of routine synthetic transformations.
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