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Merck

343641

(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
UNSPSC Code:
12352114
NACRES:
NA.22
PubChem Substance ID:
24861185
EC Number:
219-194-5
Beilstein/REAXYS Number:
1720791
MDL number:
MFCD00067089

Key Documents

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Product Name

(R)-(+)-Citronellal, technical grade

InChI key

NEHNMFOYXAPHSD-SNVBAGLBSA-N

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

SMILES string

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

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.)

functional group

aldehyde

Quality Level

100

Related Categories

Application

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

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.

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
MKCZ9071
MKCZ1900
MKCG7493
MKBZ8929V
MKBV6412V

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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
Walter S Leal et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(46), 18704-18709 (2013-10-30)
The southern house mosquito, Culex quinquefasciatus, has one of the most acute and eclectic olfactory systems of all mosquito species hitherto studied. Here, we used Illumina sequencing to identify olfactory genes expressed predominantly in antenna, mosquito's main olfactory organ. Less
Gabriele Siedenburg et al.
Applied and environmental microbiology, 78(4), 1055-1062 (2011-12-14)
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)
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%
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
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