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Citral

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

Citral Properties

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
Merck 
14,2322
JECFA Number
1225
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
2,6-Octadienal, 3,7-dimethyl-(5392-40-5)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
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)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H401 Toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 2 P273, P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P272 Contaminated work clothing should not be allowed out of the workplace.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P321 Specific treatment (see … on this label).
P308+P313 IF exposed or concerned: Get medical advice/attention.
P333+P313 IF SKIN irritation or rash occurs: Get medical advice/attention.
P405 Store locked up.
P501 Dispose of contents/container to..…

NFPA 704

Diamond Hazard Value Description
2
0
Health  
Flammability   2 Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur and multiple finely divided suspended solids that do not require heating before ignition can occur. Flash point between 37.8 and 93.3 °C (100 and 200 °F). (e.g. diesel fuel, sulfur)
Instability   0 Normally stable, even under fire exposure conditions, and is not reactive with water (e.g. helium,N2)
Special  

(NFPA, 2010)

Citral price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 15861 Citral analytical standard 5392-40-5 1ml $49.4 2018-11-13 Buy
Sigma-Aldrich 43318 Citral analytical standard 5392-40-5 1ml $51.5 2018-11-13 Buy
TCI Chemical D0762 Citral (cis- and trans- mixture) >98.0%(GC) 5392-40-5 25mL $11 2018-11-22 Buy
Alfa Aesar A16169 Citral, cis + trans, 95% 5392-40-5 50g $19.4 2018-11-13 Buy
Alfa Aesar A16169 Citral, cis + trans, 95% 5392-40-5 100g $28.5 2018-11-13 Buy

Citral Chemical Properties,Uses,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

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

mobile light yellow liquid with a lemon-like smell

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.

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.

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.

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.

Citral Preparation Products And Raw materials

Raw materials

Preparation Products


Citral Suppliers

Global( 217)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3203 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1730 55
Xiamen AmoyChem Co., Ltd
+86 (0)592-605 1114
sales@amoychem.com CHINA 6374 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 24001 58
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20095 58
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 4669 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20331 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
Jiangxi Baolin Natural Spices Co.Ltd. 0796-8102348 13576833965 13576827225
0796-8116585 1046750473@qq.com China 121 58

View Lastest Price from Citral manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-17 Citral
5392-40-5
US $1.00 / kg 1 g 99% 100KG career henan chemical co

Citral Spectrum


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