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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

Quality Level

100

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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG7493
MKBZ8929V
MKBV6412V
MKBM0881V
08214PR

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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
Lucindo José Quintans-Júnior et al.
Journal of orofacial pain, 24(3), 305-312 (2010-07-29)
To evaluate the antinociceptive effects of citronellal (CTL) on formalin-, capsaicin-, and glutamate-induced orofacial nociception in mice and to investigate whether such effects might involve a change in neural excitability. Male mice were pretreated with CTL (50, 100, and 200
Thomas Gallert et al.
ChemSusChem, 4(11), 1654-1661 (2011-08-10)
The microwave-assisted hydrogenation of citral (3,7-dimethylocta-2,6-dienal) to citronellal with molecular hydrogen as the reducing agent was investigated. Several polar and non-polar solvents were screened and imidazolium-based ionic liquids were applied as modifiers for the palladium-containing porous glass catalysts (Pd/TP). The
Ying-Fang Ting et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(23), 7030-7038 (2010-05-11)
Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7 a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical alpha,alpha-disubstituted aldehydes to beta-nitroalkenes. When this
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