7488-99-5

Basic information

• Product Name: Carotene
• Synonyms: A-CAROTENE;ALPHA/BETA-CAROTENE MIX;ALPHA-CAROTENE;CAROTENE, A-;ALPHA-CAROTENE FROM CARROTS;.beta.,.epsilon.-Carotene, (6R)-;(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1-(2,6,6-trimethyl-1-cyclohexenyl)-18-(2,6,6-trimethyl-1-cyclohex-2-enyl)octadeca-1,3,5,7,9,11,13,15,17-nonaene;CISALPHA-CAROTENE
• CAS NO: 7488-99-5
• Molecular Formula: C₄₀H₅₆
• Molecular Weight: 536.87
• EINECS: 200-838-9
• Product Categories: Miscellaneous Natural Products;CA - CGChromatography;OtherChromatography;Vitamins/CoFactors/Enzymes;Alphabetic;C;Food&Beverage Standards;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class
• Mol File: 7488-99-5.mol

Chemical Properties

• Melting Point: 187.50° (evacuated tube)
• Boiling Point: 644.94°C (rough estimate)
• Flash Point: 341.2oC
• Appearance: /
• Density: 0.9380 (estimate)
• Vapor Pressure: 8.15E-16mmHg at 25°C
• Refractive Index: 1.5630 (estimate)
• Storage Temp.: ?20°C
• Solubility: Chloroform (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• BRN: 3227603
• CAS DataBase Reference: Carotene(CAS DataBase Reference)
• NIST Chemistry Reference: Carotene(7488-99-5)
• EPA Substance Registry System: Carotene(7488-99-5)

Safety Data

• Hazard Codes: Xn
• Statements: 40-67-36/37/38
• Safety Statements: 36/37-24/25-23
• RIDADR: UN 1593 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 7488-99-5(Hazardous Substances Data)

Usage

Uses

Used in Cosmetic Industry:
Carotene is used as a colorant to provide a red-orange color in cosmetic formulations.
Used in Food Industry:
Carotene is used as a natural colorant in ice cream, cheese, and other dairy products. It is also the primary yellow coloring component of butter, carrots, and egg yolk.
Used in Health and Nutrition:
Carotene is used as a vitamin A precursor, which is converted by the body to vitamin A. It has been found to inhibit the proliferation of GOTO human neuroblastoma cells and halt the cell cycle at the G0/G1 phase, reducing the mRNA expression of the protooncogene N-Myc. It is also more potent than β-carotene in mouse models of skin and lung carcinogenesis and decreases the number of hepatomas in mice with spontaneous liver carcinogenesis when administered in drinking water at a concentration of 0.05%. Additionally, α-carotene levels are increased in patients with coronary heart disease and are inversely correlated with the risk of estrogen receptor-negative breast cancer.

Biochem/physiol Actions

One of the primary isomers of carotene, enantiomerically pure form of metabolite in carotenoid biosynthesis, biosynthesis of plant secondary metabolites, biosynthesis of terpenoids and steroids and the biosynthesis of secondary metabolites.

Purification Methods

Purify α-carotene by chromatography on columns of calcium hydroxide, alumina or magnesia. Crystallise it from CS2/MeOH, toluene/MeOH, diethyl ether/pet ether, or acetone/pet ether. Store it in the dark, under N2 or Ar at -20o. It gives a blue colour with max at 542nm when mixed with SbCl3 in CHCl3. [Karrer & Walker Helv Chim Acta 16 641 1933, Eugster et al. Helv Chim Acta 52 1729 1969, Eugster & Karrer Helv Chim Acta 38 610 1955, Strain J Biol Chem 105 523 1934, Beilstein 5 III 2457, 5 IV 2620.]

InChI:InChI=1/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1

Upstream product

• 124159-69-9 dl-15,15'-Dehydro-α-carotin 
• 16910-82-0 15,15'-didehydro-12'-apo-β-caroten-12'-al 
• 50876-26-1 (E,E,E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-enyl)octa-2,4,6-trienal 
• 26533-79-9 Ethinyl-α-ionol 
• 127-41-3 alpha-ionone 
• 432-70-2 9-cis-α-carotene 
• 7553-56-2 iodine 
• 125069-77-4 (E)-4-octene-2,7-dione 
• 74352-11-7 6-(2-methyl-6,6-dimethylcyclohex-1-en-1-yl)-3-methylhex-1-ene-5-yne-3-ol 
• 6060-33-9 1,3,3-Trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-cyclohexanol 
• 79-77-6 (E)-β-ionone 
• 127-40-2 lutein 
• 15678-54-3 mutatochrome 

Downstream Products

• 3297-23-2 α-echinenone 
• 61825-48-7 (4Ξ,6'R)-β,ε-caroten-4-ol 
• 122704-30-7 (4Ξ,6'R)-4-methoxy-β,ε-carotene 
• 122569-68-0 (4Ξ,6'R)-4-ethoxy-β,ε-carotene 
• 3484-56-8 2,3,2',3',4',5'-hexadehydro-4,5'-retro-β,β-carotene 
• 752-24-9 3,4,3',4'-tetradehydro-β,β-carotene 
• 13761-10-9 retro-bisdehydrocarotene 
• 68-26-8 RETINOL 
• 124383-25-1 (4Ξ,6'R)-4-acetoxy-β,ε-carotene 
• 7235-40-7 beta-carotene 
• 432-70-2 9-cis-α-carotene 
• 471-04-5 4,4-dimethyl-6-oxo-heptanoic acid 
• 2790-54-7 all-trans-5,6-dihydro-β-carotene 
• 2423-77-0 all-trans-5,6-dihydro-α-carotene 

Relevant articles and documents

Artificially coloring the skin with a carotene compound, a xanthophyll compound and a lipophilic green dye composition

A method for artificially coloring the skin entails topical application thereon of a composition containing, formulated into a physiologically acceptable medium: a) at least one compound of the carotene type,b) at least one compound of the xanthophyll type,c) at least one lipophilic green dye; the composition advantageously includes a mixture of dyes including:a) at least one compound of the carotene type,b) at least astaxanthin,c) at least one lipophilic green dye.

Kinetic Model for Studying the Isomerization of α- and β-Carotene during Heating and Illumination

The thermoisomerization and iodine-catalyzed photoisomerization of all-trans-α- and all-trans-β-carotene were kinetically studied using regression models. Carotene samples were heated at varied temperatures or exposed to a 20 W light for varied lengths of time. Isomerization and degradation reactions were monitored using HPLC with diode array detection. Four cis isomers of β-carotene and three cis isomers of α-carotene were separated and detected. The degradations of both carotenes under heating at 150 deg C or iodine/light treatment may fit the reversible first- order model. 9-cis and 13-cis were the major β-carotene isomers formed during heating, while 13,15-di-cis was favored during iodine-catalyzed photoisomerization. The formation of 9-cis and 13-cis form all-trans-α-carotene was dependent upon the extent of heat or iodine/light treatment, and the latter was formed in greater amount under either treatment. Keywords: α-Carotene; β-carotene; thermoisomerization; photoisomerization; kinetic study