(-)-CITRONELLAL

(-)-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

(-)-CITRONELLAL Chemical Properties

Boiling point	227.64°C (estimate)
density	0.851 g/mL at 20 °C (lit.)
refractive index	n20/D 1.447
Fp	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)

Safety Information

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

MSDS Information

Provider	Language
SigmaAldrich	English

(-)-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.]

(-)-CITRONELLAL Preparation Products And Raw materials

Raw materials	(+)-ISOPULEGOL-->(Z)-3,7-dimethylocta-2,6-dienal-->2,6-dimethylhepta-1,5-diene-->(+)-CITRONELLAL-->trans-Citral = trans-3,7-Dimethyl-octa-2,6-dien-1-al-->carbon monoxide-->Citral-->NEROL
Preparation Products	BETA-RHODINOL

PHORBOL 12-MYRISTATE 13-ACETATE 4-O-METHYL ETHER, 4BETA PHORBOL 13-ACETATE PHORBOL-12-MONOMYRISTATE Dehydroepiandrosterone DEHYDROANDROSTERONE ACETATE PHORBOL 12-MYRISTATE 13-ACETATE PHORBOL 12,13-DIACETATE 20-OXO-20-DEOXYPHORBOL 12,13-DIBUTYRATE PHORBOL 12,13-DIBUTYRATE PHORBOL 12,13-DIBENZOATE Sodium prasterone sulfate PHORBOL 12-MONOACETATE, 4BETA PHORBOL, 20-OXO-20-DEOXY 12-MYRISTATE 13-ACETATE, 4BETA PHORBOL-12-DECANOATE 4ALPHA-PHORBOL PHORBOL 12,13,20-TRIACETATE, 4BETA 3beta-(methoxymethoxy)androst-5-en-17-one PHORBOL 13,20-DIACETATE

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