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(-)-CITRONELLAL

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(-)-CITRONELLAL Basic information

Product Name:
(-)-CITRONELLAL
Synonyms:
  • (S)-(-)-Citronellal 96%
  • L(-)-Citronellal
  • CITRONELLAL(L-)
  • (3S)-3,7-dimethyl-6-Octenal
  • (-)-CITRONELLAL WITH GC
  • (S)-(-)-3,7-DIMETHYL-6-OCTENAL
  • (S)-3,7-DIMETHYL-6-OCTENAL
  • (S)-(-)-CITRONELLAL
CAS:
5949-05-3
MF:
C10H18O
MW:
154.25
EINECS:
227-707-9
Product Categories:
  • Asymmetric Synthesis
  • Building Blocks
  • C10-C12
  • Carbonyl Compounds
  • Chemical Synthesis
  • Chiral Building Blocks
  • Acyclic Monoterpenes
  • Biochemistry
  • Citrus aurantium (Seville orange)
  • Elettaria Cardamomum (Cardamom)
  • Nutrition Research
  • Organic Building Blocks
  • Phytochemicals by Plant (Food/Spice/Herb)
  • Zingiber officinale (Ginger)
  • Terpenes
  • Aldehydes
Mol File:
5949-05-3.mol
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(-)-CITRONELLAL Chemical Properties

Boiling point:
227.64°C (estimate)
Density 
0.851 g/mL at 20 °C (lit.)
refractive index 
n20/D 1.447
Flash point:
168 °F
storage temp. 
Hygroscopic, Refrigerator, under inert atmosphere
solubility 
Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
Oil
color 
Colourless
Odor
at 10.00 % in dipropylene glycol. clean herbal citrus
Odor Type
citrus
optical activity
[α]20/D 15°, neat
BRN 
1720790
LogP
3.482 (est)
CAS DataBase Reference
5949-05-3(CAS DataBase Reference)
EPA Substance Registry System
6-Octenal, 3,7-dimethyl-, (3S)- (5949-05-3)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
10-23
HS Code 
29121900

MSDS

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(-)-CITRONELLAL Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO PALE YELLOW LIQUID

Uses

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

Definition

ChEBI: The (3S)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).

General Description

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

Purification Methods

Fractionally distil it. Alternatively extract it with NaHSO3 solution, wash it with Et2O, then acidify it to decompose the bisulfite adduct and extract with Et2O, dry (Na2SO4), evaporate and distil. Check for purity by hydroxylamine titration. The ORD in MeOH (c 0.167) is: []700 +9o, []589 +11o, []275 +12o and []260 +12o. The semicarbazone has m 85o, and the 2,4-dinitrophenylhydrazone has m 79-80o. [(+)-compound: Tietze & Beifuss Org Synth 71 167 1993, IR: Carroll et al. J Chem Soc 3457 1950, ORD: Djerassi & Krakower J Am Chem Soc 81 237 1959, Beilstein 1 IV 3515.]

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