(-)-CITRONELLAL

Synonym(s):(−)-Citronellal;(3S)-3,7-Dimethyl-6-octenal

CAS NO.：5949-05-3
Empirical Formula: C10H18O
Molecular Weight: 154.25
MDL number: MFCD00075588
EINECS: 227-707-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:15:32

What is (-)-CITRONELLAL?

Chemical properties

CLEAR COLOURLESS TO PALE YELLOW LIQUID

The Uses of (-)-CITRONELLAL

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

What are the applications of Application

(S)-(–)-Citronellal is a monoterpenoid responsible for the aroma of kaffir lime oil

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.]

Properties of (-)-CITRONELLAL

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
optical activity	[α]20/D 15°, neat
BRN	1720790
CAS DataBase Reference	5949-05-3(CAS DataBase Reference)
EPA Substance Registry System	6-Octenal, 3,7-dimethyl-, (3S)- (5949-05-3)

Safety information for (-)-CITRONELLAL

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.