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:
Molecular Weight:
154.25
Beilstein:
1720791
EC Number:
MDL number:
UNSPSC Code:
12352114
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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
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
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.
Signal Word
Warning
Hazard Statements
Precautionary 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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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)
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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)
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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%
M S Melo et al.
Pharmaceutical biology, 48(4), 411-416 (2010-07-22)
Citronellal is a monoterpene reported to be a major component of the essential oils in various aromatic species of plants. The present study evaluated the central nervous system depressant and antinociceptive properties of citronellal through behavioral experimental models. Following intraperitoneal
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