Overview Toxicity Usage limits Chemical Properties Application Production method
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Citral

Overview Toxicity Usage limits Chemical Properties Application Production method
Product Name
Citral
CAS No.
5392-40-5
Chemical Name
Citral
Synonyms
NERAL;CITRAL;LEMSYN;lemsyngb;b-citral;citral b;a-citral;gerznial;GERANIAL;LEMAROME
CBNumber
CB8364074
Molecular Formula
C10H16O
Formula Weight
152.23
MOL File
5392-40-5.mol
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Citral Property

Melting point:
<-10°C
Boiling point:
229 °C (lit.)
Density 
0.888 g/mL at 25 °C (lit.)
vapor density 
5 (vs air)
vapor pressure 
0.2 mm Hg ( 200 °C)
refractive index 
n20/D 1.488(lit.)
FEMA 
2303 | CITRAL
Flash point:
215 °F
storage temp. 
2-8°C
solubility 
0.42g/l
form 
Liquid
color 
colorless to light yellow
explosive limit
4.3-9.9%(V)
Water Solubility 
PRACTICALLY INSOLUBLE
JECFA Number
1225
Merck 
14,2322
BRN 
1721871
Stability:
Stable. but readily isomerizes. Incompatible with alkalies, strong oxidizing agents, strong acids. Combustible. Air and light sensitive.
CAS DataBase Reference
5392-40-5(CAS DataBase Reference)
NIST Chemistry Reference
Citral(5392-40-5)
EPA Substance Registry System
Citral (5392-40-5)
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Safety

Hazard Codes 
Xi
Risk Statements 
38-43
Safety Statements 
24/25-37
RIDADR 
1760
WGK Germany 
1
RTECS 
RG5075000
Autoignition Temperature
225 °C
TSCA 
Yes
HS Code 
2912 19 00
HazardClass 
8
PackingGroup 
III
Hazardous Substances Data
5392-40-5(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 4.96 g/kg (Opdyke)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H361Suspected of damaging fertility or the unborn child

H401Toxic to aquatic life

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P321Specific treatment (see … on this label).

P308+P313IF exposed or concerned: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.02489
Product name
Citral
Purity
(mixture of cis- and trans-isomers) for synthesis
Packaging
5 mL
Price
$24.05
Updated
2021/03/22
Sigma-Aldrich
Product number
15861
Product name
Citral
Purity
analytical standard
Packaging
1ml
Price
$54
Updated
2021/03/22
Sigma-Aldrich
Product number
43318
Product name
Citral
Purity
analytical standard
Packaging
1ml
Price
$56.2
Updated
2021/03/22
Sigma-Aldrich
Product number
8.02489
Product name
Citral
Purity
(mixture of cis- and trans-isomers) for synthesis
Packaging
250 mL
Price
$91.57
Updated
2021/03/22
Sigma-Aldrich
Product number
W230308
Product name
Citral
Purity
mixture of cis and trans, ≥96%, FG
Packaging
1 kg
Price
$95
Updated
2021/03/22
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Citral Chemical Properties,Usage,Production

Overview

Citral (C10H16O), also called 3,7-dimethyl-2,6-octadienal, a pale yellow liquid, with a strong lemon odour, that occurs in the essential oils of plants. It is insoluble in water but soluble in ethanol (ethyl alcohol), diethyl ether, and mineral oil. It is used in perfumes and flavourings and in the manufacture of other chemicals. Chemically, citral is a mixture of two aldehydes that have the same molecular formula but different structures.
Content analysis
Accurately weigh about 1g of the sample, and then perform the determination by the hydroxylamine method (OT-7, method one) used in aldehyde and ketone determination. The equivalent factor (e) in the calculation is 76.12.

Toxicity

ADI 0~0.5mg/kg (FAO/WHO, 1994-). LD50 4960 mg/kg (rat, oral); MNL 500 mg/kg.

Usage limits

FEMA (mg/kg): soft drinks 9.2; cold drinks 23; candy 41; baked goods 43; chewing gums 170

Chemical Properties

Colorless or slightly yellow liquid; strong lemon flavor; no optical rotation; boiling point 228 °C; flash point 92 °C;
There are cis and trans two isomers. With sodium bisulfite treatment, cis isomer solubility is minimal, while the trans isomer solubility is very large, so the two isomers can be separated.
Cis citral: relative density (d20) 0.8898, refractive index (nD20) 1.4891, boiling point 118~119℃ (2666Pa).
Trans citral: relative density (d20) 0.8888, refractive index (nD20) 1.4891, boiling point 117~118℃ (2666Pa).
Soluble in non-volatile oils, volatile oils, propylene glycol and ethanol; insoluble in glycerol and water; unstable in alkaline and strong acids
Natural products present in lemon grass oil (70% to 80%), litsea cubeba oil (about 70%), lemon oil, white lemon oil, citrus leaf oil and so on.

Application

Citral is an artificial flavor permitted to use in China, which can be used to prepare strawberries, apples, apricots, sweet orange, lemon and other fruit-based flavors. According to normal production needs, the citrals amount used in chewing gums is 1.70mg/kg; baked goods 43mg/kg; candy 41mg/kg; cold drinks 23mg/kg; soft drinks 9.2mg/kg.
It is also widely used in dishwashing detergents and the flavoring agents of soap and toilet water. Citral can be used as the raw material to synthesize ionone, methyl ionone and dihydro damascene. As organic raw material, it can also be reduced to generate citronellol, nerol alcohol and geraniol, and be converted into lemonile. In the pharmaceutical industry, it can be used for the manufacture of vitamin A and E, and also as the raw material of chlorophyll.

Production method

Citral natural exists in the litsea cubeba oil (about 80%), lemon grass oil (80%), clove basil oil (65%), sour lemon oil (35%) and lemon oil. In industry, citral can be derived from natural essential oils, or be prepared by chemical.
Synthesis based on methyl heptenone as raw material
Ethoxyacetylene magnesium bromide and methyl heptenone performed condensation reaction to form 3,7-dimethyl-1-ethoxy-3-hydroxy-6-octene-1-yne, which was then partly hydrogenated in the presence of catalysis to generate enol ether. And the enol ether was then hydrolyzed with phosphoric acid and dehydrated to obtain citral, with a yield of 68% calculated by methyl heptenone. In addition, acetylene and methyl heptenone could perform condensation reaction to form dehydrogenation linalool, which was then rearranged in the presence of silicon sulfone catalysis at 140~150 °C in inert solvent to get citral.
Derived from litsea cubeba oil (which is the main method to product citral in China)
Add 30 kg of cubeba oil containing about 75% of citral into a mixture under fully stirring, which was prepared with 18 kg of sodium bicarbonate, 38 kg of sodium sulfite and about 165 kg of water, and then continually stir for 5 to 6 h at room temperature. After standing overnight for stratification, the lower citral precipitated in the form of adduct. And the adduct was then washed with a small amount of toluene to remove oil and dried. And then add 10% sodium hydroxide solution to decompose citral at room temperature, and extract it with benzene. The extract was first distilled at atmospheric pressure (80-82°C) to recover benzene and then distilled under reduced pressure to collect fractions of 110-111°C (1.47kPa) to obtain pure product of 98% citral in an amount of about 15 to 16 kg.

Chemical Properties

mobile light yellow liquid with a lemon-like smell

Chemical Properties

Citral occurs as (2Z)- and (2E)-isomers (citral a and b, respectively) analogous to the corresponding alcohols, geraniol and nerol: geranial (citral a), bp2.7 kPa 118–119 °C, d20 0.8888, n20 D 1.4898; neral (citral b), bp2.7 kPa 120 °C, d20 0.8869, n20 D 1.4869. Natural citral is nearly always a mixture of the two isomers. It occurs in lemongrass oil (up to 85%), in Litsea cubeba oil (up to 75%), and in small amounts inmany other essential oils. The citrals are colorless to slightly yellowish liquids, with an odor reminiscent of lemon.
Since citral is an α,β-unsaturated aldehyde with an additional double bond, it is highly reactive and may undergo reactions such as cyclization and polymerization. Geraniol, citronellol, and 3,7-dimethyloctan-l-ol can be obtained from citral by stepwise hydrogenation. Citral can be converted into a number of addition compounds; the (Z)- and (E)-isomers can be separated via the hydrogen sulfite addition compounds.The condensation of citral with active methylene groups is used on an industrial scale in the synthesis of pseudoionones, which are starting materials for ionones and vitamins.

Chemical Properties

Citral has a strong, lemon-like odor and a characteristic bittersweet taste. Commercially, the product is a mixture of two geometric isomers—α-citral and β-citral, each exhibiting cis- and trans-isomers because of the position of the double bond.

Occurrence

Reported found in apricot, clary sage, ginger, grape, grapefruit, lemon, lime, mandarin, orange, raspberry, tamarind, tangerine, tea and tomato.

Uses

Citral is a liquid flavoring agent, light yellow in color with a citrus odor. it occurs in lemon and lemongrass oils. it is usually obtained from citral-containing oils by chemical means but may also be pre- pared synthetically. it is soluble in fixed oils, mineral oil, and pro- pylene glycol. it is moderately stable and should be stored in glass, tin, or resin-lined containers. it is used in flavors for lemon with applications in candy, baked goods, and ice cream at 20–40 ppm. it is also termed 2,6-dimethyl-octadian-2-6-al-8.

Uses

Citral is an anti-microbial agent found in plants with antibacterial activity against some food pathogens. It is also a fragrance compound with a distinct lemon scent.

Uses

citral is a naturally occurring aroma compound used to provide a lemon-type fragrance. Citral is a constituent of lemon oil, lemongrass oil, lime oil, ginger oil, verbena oil, and other plant-derived C essential oils.

Preparation

Since citral is used in bulk as a starting material for the synthesis of vitamin A, it is produced industrially on a large scale. Smaller quantities are also isolated from essential oils.
1) Isolation from essential oils: Citral is isolated by distillation from lemongrass oil and from L. cubeba oil. It is the main component of these oils. 2) Synthesis from geraniol: Currently, the most important synthetic procedures are vapor-phase dehydrogenation and oxidation of geraniol or geraniol–nerol mixtures. Catalytic dehydrogenation under reduced pressure using copper catalysts is preferred.
3) Synthesis from dehydrolinalool: Dehydrolinalool is produced on a large scale from 6-methyl-5-hepten-2-one and acetylene and can be isomerized to citral in high yield by a number of catalysts. Preferred catalysts include organic orthovanadates, organic trisilyl oxyvanadates, and vanadium catalysts with silanols added to the reaction system.
4) Synthesis from isobutene and formaldehyde: 3-Methyl-3-buten-l-ol, obtained from isobutene and formaldehyde, isomerizes to form 3-methyl- 2-buten-lol. However, it is also converted into 3-methyl-2-butenal by dehydrogenation and subsequent isomerization. Under azeotropic conditions in the presence of nitric acid, 3-methyl-2-buten-l-ol and 3-methyl-2-butenal form an acetal (shown as follows), which eliminates one molecule of 3-methyl-2-buten-l-ol at higher temperatures. The intermediate enol ether undergoes Claisen rearrangement followed by Cope rearrangement to give citral in excellent yield:
Today, this route is performed on a very large industrial scale in a continuous reactive distillation process.

Definition

Commercial material is a mixture of α and β isomers.

Aroma threshold values

Detection at 1.0%: characterizing lemon-like, distilled lime peel, intense aldehydic citruslike.

Taste threshold values

Taste characteristics at 5 ppm in 5% sugar and 0.1% CA: characteristic lemon, peely, citrus, green floral juicy with woody and candy notes.

Synthesis Reference(s)

Journal of the American Chemical Society, 101, p. 7131, 1979 DOI: 10.1021/ja00517a088
Tetrahedron Letters, 35, p. 4007, 1994 DOI: 10.1016/S0040-4039(00)76726-8

General Description

A clear yellow colored liquid with a lemon-like odor. Less dense than water and insoluble in water. Toxic by ingestion. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Citral is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Citral can react with alkalis and strong acids. Citral can readily isomerize.

Hazard

Questionable carcinogen.

Fire Hazard

Citral is combustible.

Contact allergens

Citral is an aldehyde fragrance and flavoring ingredient, a blend of isomers cis (Neral) and trans (geranial). As a fragrance allergen, citral has to be mentioned by name in cosmetics within the EU.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Experimental reproductive effects. A severe human and experimental skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Chemical Synthesis

Citral is usually isolated from the citral-containing oil by chemical means or by chemical synthesis (from β-pinene, isoprene, etc.).

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Citral Suppliers

Jishui County Yikang Natural Flavor Oil Refinery
Tel
0796-8128936
Fax
0796-8128936
Email
201999698@qq.com
Country
China
ProdList
159
Advantage
58
Shanghai Jiulin Industrial Co., Ltd.
Email
956247821@qq.com
Country
CHINA
ProdList
301
Advantage
58
Jiangxi Xinsen Natural Vegetable Oil Co., Ltd.
Tel
0796-8284836-
Fax
0796-8284836
Email
592432494@qq.com;
Country
China
ProdList
200
Advantage
58
Ji 'an trillion spice oil co. LTD
Tel
0796-8110986
Email
1053756189@qq.com
Country
China
ProdList
90
Advantage
58
Jiangxi Baolin Natural Spices Co.Ltd.
Tel
0796-8180428-
Fax
0796-8116585
Email
1510355607@qq.com
Country
China
ProdList
118
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
Beijing dtftchem Technology Co., Ltd.
Tel
13651141086; 86(10)60275028、60275820
Fax
86 (10) 60270825
Email
dtftchem@sina.com
Country
China
ProdList
3392
Advantage
62
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View Lastest Price from Citral manufacturers

Wuhan Mulei New Material Technology Co. Ltd
Product
Citral 5392-40-5
Price
US $10.00/KG/Tin
Min. Order
1KG
Purity
99%
Supply Ability
5000tons per month
Release date
2021-04-01
Wuhan Monad Medicine Tech Co.,LTD
Product
2,6-Octadienal,3,7-dimethyl- 5392-40-5
Price
US $50.00/KG
Min. Order
1Kg/Bag
Purity
99.99%
Supply Ability
20 tons/month
Release date
2021-04-19
Hebei Crovell Biotech Co Ltd
Product
Citral 5392-40-5
Price
US $10.00/KG/CTN
Min. Order
10g
Purity
99 %
Supply Ability
10000kg
Release date
2021-06-24

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