5392-40-5
Citral, mixture of cis and trans
CAS: 5392-40-5
Molecular Formula: C10H16O
5392-40-5 - Names and Identifiers
| Name | Citral, mixture of cis and trans |
| Synonyms | Citral linmengquan Citralcistrans cis,trans-Citral Citral synthetic citral (cis+trans) Citral Extra. nat. 6-Octadienal,3,7-dimethyl-2 3,7-Dimethyl-2,6-octadienal 3,7-Dimethyll-2,6-octadienal 2,6-Octadienal,3,7-dimethyl- 3,7-dimethyl-octa-2,6-dienal 2,6-Octadienal, 3,7-dimethyl- 3,7-Dimethyl-1,2,6-octadienal Citral, mixture of cis and trans |
| CAS | 5392-40-5 |
| EINECS | 226-394-6 |
| InChI | InChI=1/2C10H16O/c2*1-9(2)5-4-6-10(3)7-8-11/h2*5,7-8H,4,6H2,1-3H3/b10-7+;10-7- |
5392-40-5 - Physico-chemical Properties
| Molecular Formula | C10H16O |
| Molar Mass | 152.23 |
| Density | 0.888 g/mL at 25 °C (lit.) |
| Melting Point | <-10°C |
| Boling Point | 229 °C (lit.) |
| Specific Rotation(α) | n20/D 1.488 (lit.) |
| Flash Point | 215°F |
| JECFA Number | 1225 |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Solubility | Soluble in organic solvents such as ethanol, acetone, ethyl acetate, etc., insoluble in water and glycerol |
| Vapor Presure | 0.2 mm Hg ( 200 °C) |
| Vapor Density | 5 (vs air) |
| Appearance | Transparent to light yellow oily liquid |
| Color | colorless to light yellow |
| Exposure Limit | ACGIH: TWA 5 ppm (Skin) |
| Merck | 14,2322 |
| BRN | 1721871 |
| Storage Condition | 2-8°C |
| Stability | Stable. but readily isomerizes. Incompatible with alkalies, strong oxidizing agents, strong acids. Combustible. Air and light sensitive. |
| Sensitive | `sensitive` to light, heat and air |
| Explosive Limit | 4.3-9.9%(V) |
| Refractive Index | n20/D 1.488(lit.) |
| MDL | MFCD00006997 |
| Physical and Chemical Properties | Colorless or yellowish liquid with rich lemon flavor. No optical rotation. Boiling point 228 degrees C, flash point 92 degrees Celsius. There are two kinds of cis and trans isomers. With sodium bisulfite treatment, the CIS solubility is very small, while the trans is very large, so that the two can be separated. Cis-citral: Relative density (d200.8898, refractive index (nD20)1.4891, boiling point 118~119 ℃(2666Pa). Trans citral: Relative density 0.8888, refractive index (nD20)1.4891, boiling point 117~118 ℃(2666Pa). Soluble in non-volatile oil, volatile oil, propylene glycol and ethanol, insoluble in glycerol and water. Unstable in alkaline and strong acids. Natural products are found in lemon grass oil (70%-80%), Litsea cubeba oil (about 70%), lemon oil, lime oil, citrus leaf oil, etc. |
| Use | Used as a flavoring agent, the preparation of lemon flavor, also used as a raw material for the synthesis of ionone and vitamin A |
5392-40-5 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R38 - Irritating to the skin R43 - May cause sensitization by skin contact |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S37 - Wear suitable gloves. |
| UN IDs | 1760 |
| WGK Germany | 1 |
| RTECS | RG5075000 |
| TSCA | Yes |
| HS Code | 2912 19 00 |
| Hazard Class | 8 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 4.96 g/kg (Opdyke) |
5392-40-5 - Reference
| Reference Show more | 1. Peng Xianglian, Cai Zhilin, Fu Red Army. Separation and Purification of citral from the essential oil of litsea cubeba [J]. Forestry industry, 2018, v.45;No.276(08):21-26. 2. Dong Xiaoke, Liu Jinmin, Li Zhonghao, Yuan Siyuan, Wang Kaiyue, Li Lili, Zheng xiangchun. Study on the main blood components and pharmacokinetics of chaibei Zhixian decoction in rats [J]. Global Journal of Traditional Chinese Medicine, 2021,14(03):377-383. 3. Qian, Weidong, et al. "Antimicrosal and antibiofilm activities of systemic against carbapenem-resistant Enterobacter cloacae." Foodborne pathogens and disease 17.7 (2020): 459-465.https:// doi.org/10.1089/fpd.2019.2751 4. Liu, Huang, et al. "Antimicrobial activity and virulence attenuation of citral against the fish pathogen Vibrio alginolyticus." Aquaculture 515 (2020): 734578.https://doi.org/10.1016/j.aquaculture.2019.734578 5. [IF=5.548] Juanjuan Cao et al."Antimicrobial and antivirulence efficacies of citral against foodborne pathogen Vibrio parahaemolyticus RIMD2210633."Food Control. 2021 Feb;120:107507 6. [IF=4.952] Yuxiang Zhang et al."Antibacterial activity of essential oils against Stenotrophomonas maltophilia and the effect of citral on cell membrane."Lwt Food Sci Technol. 2020 Jan;117:108667 7. [IF=4.242] Huan Liu et al."Antimicrobial activity and virulence attenuation of citral against the fish pathogen Vibrio alginolyticus."Aquaculture. 2020 Jan;515:734578 8. [IF=4.24] Weiyun Bi et al."Preventive effect of different citrus essential oils on primary dysmenorrhea: in vivo and in vitro study."Food Biosci. 2021 Aug;42:101135 |
5392-40-5 - Nature
Open Data Verified Data
A colorless to yellowish oily liquid with a strong lemon odor. The relative density is 0. 884~0.886(20 ℃). Boiling point 228~229 deg C. Ignition point: 92 ℃. Refractive index 1. 485 to 1. 491 (20 °c). Volatile, insoluble in water, 10 times soluble in 60% ethanol, soluble in propylene glycol, benzyl benzoate, phthalate Diethyl ester, mineral oil, esters and chloroform, insoluble in glycerol.
Last Update：2024-01-02 23:10:35
5392-40-5 - Preparation Method
Open Data Verified Data
vacuum distillation method or chemical method is used to extract from litsea cubeba oil (fruit of litsea cubeba can be obtained by steam distillation 3% ~ 5% of the essential oil).
Last Update：2022-01-01 10:16:45
5392-40-5 - Use
Open Data Verified Data
mainly used for the synthesis of ionone, dihydrodamazone and other spices; As organic raw materials can be reduced to citronellol, nerol and geraniol; Can also be converted into citronitrile. Used in the pharmaceutical industry for the manufacture of vitamins A and E.
Last Update：2022-01-01 10:16:46
5392-40-5 - Safety
Open Data Verified Data
Toxicity: The oral LD50 of rats was 4960mg/kg. lOkg or 25kg plastic barrel packaging. Store in a cool, ventilated warehouse, away from heat sources and fire.
Last Update：2022-01-01 10:16:46
5392-40-5 - Reference Information
| FEMA | 2303 | CITRAL |
| LogP | 2.76 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| content analysis | accurately weigh about 1g of sample, and then proceed according to hydroxylamine method (OT-7, method 1) in aldehyde and ketone determination method. The equivalent factor (e) in the calculation is 76.12. |
| toxicity | ADI 0~0.5 mg/kg(FAO/WHO,1994-). LD50 4960mg/kg (rat, oral);MNL 500mg/kg |
| usage limit | FEMA(mg/kg): soft drink 9.2; Cold drink 23; Candy 41; Baked food 43; Gum sugar 170. |
| use | GB 2760-96 specifies edible spices that are allowed to be used. It is mainly used to prepare lemon, citrus and assorted fruit flavors, and is also the main raw material for the synthesis of ionone. It is used as a perfuming agent to prepare lemon essence, and also as a raw material for the synthesis of ionone and vitamin A It has a wide range of uses and is used in all aspects that require lemon flavor. It is an important spice for lemon type, deodorant wood type essence, artificial preparation of lemon oil, bergamot oil and orange leaf oil. It is the raw material for the synthesis of violet ketones and methyl ionones. It can also be used to cover up the bad atmosphere in industrial production. It can also be used for edible flavors such as ginger, lemon, white lemon, sweet orange, round pomelo, apple, cherry, grape, strawberry and spicy flavor. Wine flavors are also available. citral is a edible spice allowed in our country. it can be used to prepare strawberry, apple, apricot, sweet orange, lemon and other fruit flavors. The dosage is 1.70 mg/kg in gummy sugar according to the normal production requirements. 43 mg/kg in baked food; 41 mg/kg in candy; 23 mg/kg in cold drinks; 9.2 mg/kg in soft drinks. It is used for the preparation of artificial lemon oil and citrus oil, as well as other citrus spices, fruit flavors, cherries, coffee, plums and other foods. It is also widely used as detergent for tableware, soap and toilet water. Citral is a raw material for the synthesis of ionone, methyl ionone, dihydrodamagone, etc.; as an organic raw material, it can be reduced to citronellol, nerol and geraniol; it can also be converted into limononitrile. It is used in the pharmaceutical industry to make vitamins A and E, and it is also the raw material of chloroplast alcohol. synthetic vitamin a. Spices. |
| production method | naturally exists in lemongrass oil, lemon oil, white lemon oil, citrus oil, Litsea cuba oil and verbena oil. The natural essential oils of lemongrass oil and Litsea cubeba oil contain 70-80%, which can be obtained by temperature distillation from essential oils. If it is necessary to make fine products, it can be purified by sodium bisulfite method and then distilled under reduced pressure. The method of synthesizing citral in industry is based on the synthesis of methyl heptenone, and 3, 7-dimethyloctene-6-acetyl-1-ol-3 (dehydrolinalool) is made from methyl heptenone and acetylene. Then, in the presence of polymerized silicone sulfone catalyst, dehydrolinalool is directly rearranged in an inert solvent at 140-150°C. In addition, citral can be prepared by dehydrogenation of industrial geraniol (and nerol) with copper catalyst under reduced pressure gas phase. citral naturally exists in Litsea cubeba oil (about 80%), lemongrass oil (80%), clove basil oil (65%), sour lemon leaf oil (35%) and lemon oil. it can be obtained from natural essential oil in industry or prepared by chemical synthesis. Synthesis of ethoxyacetylene magnesium bromide using methyl heptenone as raw material Condensation with methyl heptenone to form 3, 7-dimethyl-1-ethoxy-3-hydroxy-6-octene-1-yne, partial catalytic hydrogenation to obtain enol ether, the latter is hydrolyzed and dehydrated with phosphoric acid to obtain citral, and the yield is 68% based on methyl heptenenone. Dehydrolinalool can also be prepared by the condensation of acetylene and methyl heptenone, and then under the catalysis of condensed silicon sulfone, citral can be redischarged at 140~150 ℃ and inert solvent. Separation from Litsea cubeba oil (this is the main method for producing citral in China) 30kg of Litsea cubeba oil containing about 75% of citral is added into a mixed solution prepared in advance by 18kg of sodium bicarbonate, 38kg of sodium sulfite and about 165kg of clear water under full stirring, and the reaction is stirred at room temperature for 5~6h. Let stand overnight to layer, and the lower citral precipitates in the form of adducts. Wash the adducts with a small amount of toluene to remove oil and spin dry. Then add 10% sodium hydroxide solution, decompress citral at room temperature, and extract with benzene. The extract is first distilled to recover benzene under normal pressure (80~82 ℃), then distilled under reduced pressure to collect fractions at 110~111 ℃(1.47kPa) to obtain 98% citral pure product of about 15~16kg. It is separated from lemongrass oil or Litsea cubeba oil by fractionation or bisulfite method. It is obtained by oxidation of geraniol, nerol or linalool under the catalysis of chromic acid. |
| spontaneous combustion temperature | 225°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:48:19
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