| Identification | Back Directory | [Name]
Carotene | [CAS]
7488-99-5 | [Synonyms]
C05433
Carotene
α-Carotene
A-CAROTENE
Renieratene
CAROTENE, A-
ALPHA-CAROTENE
Isorenieratene
CISALPHA-CAROTENE
(6’R)-,e-Carotene
Carotene USP/EP/BP
(6'R)-β,ε-Carotene
-Carotene(natural)
(6'R)-b,e-Carotene
α-Carotene Standard
TRANSALPHA-CAROTENE
R(+)-alpha-Carotene
α-Carotene Standard
α-Carotene solution
β,ε-Carotene, (6'R)-
all-trans-a-Carotene
ALPHA/BETA-CAROTENE MIX
(6'R)-beta,epsilon-carotene
ALPHA-CAROTENE FROM CARROTS
CAROTENE,ALPHA-(SH)(PLEASECALL)
.beta.,.epsilon.-Carotene, (6R)-
CAROTENE, ALPHA- 0.66mg/mL(CHLOROFORM)(SH)
CAROTENE, ALPHA- (1.0Mg/ML)(DICHLOROMETHANE)(SH)
(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 | [EINECS(EC#)]
200-838-9 | [Molecular Formula]
C40H56 | [MDL Number]
MFCD00136012 | [MOL File]
7488-99-5.mol | [Molecular Weight]
536.87 |
| Chemical Properties | Back Directory | [Melting point ]
187.50° (evacuated tube) | [alpha ]
18643 +385° (c = 0.08 in benzene) | [Boiling point ]
644.94°C (rough estimate) | [density ]
0.9380 (estimate) | [refractive index ]
1.5630 (estimate) | [storage temp. ]
?20°C | [solubility ]
Chloroform (Slightly) | [form ]
neat | [color ]
Orange to Very Dark Orange | [Odor]
Slight characteristic | [Optical Rotation]
〔α〕 643.5 +38518 (c 0.08, C6H6) | [λmax]
λ: 445-449 nm Amax | [BRN ]
3227603 | [Stability:]
Light Sensitive, Temperature Sensitive | [InChIKey]
ANVAOWXLWRTKGA-MBKINWJBNA-N | [SMILES]
C(/[C@H]1C(=CCCC1(C)C)C)=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(CCCC1(C)C)C |&1:1,r| | [Uses]
Carotene is a colorant and provitamin, being a hydrocarbon which is
one of two subgroups of the carotenoids (yellow, orange, or red pig-
ments). the other subgroup is xanthophylls. functions as
a colorant with beta-apo-8-carotenal being a red-orange carotenoid
and betabeing a yellow carotenoid. it is also a vitamin a
precursor that is converted by the body to vitamin a. it is used in ice
cream, cheese, and other dairy products. |
| Hazard Information | Back Directory | [Description]
α-Carotene is a precursor of vitamin A (Item No. 20241) that has been found in various fruits and vegetables.1 It inhibits proliferation of GOTO human neuroblastoma cells more potently than β-carotene (Item No. 16837) and halts the cell cycle at the G0/G1 phase concomitantly with a reduction in the mRNA expression of the protooncogene N-Myc.2 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%.3 α-Carotene levels are increased in patients with coronary heart disease and are inversely correlated with the risk of estrogen receptor-negative breast cancer.4,5 | [Definition]
ChEBI: (6'R)-beta,epsilon-carotene is an alpha-carotene. It is an enantiomer of a (6'S)-beta,epsilon-carotene. | [General Description]
α-Carotene is a carotenoid, which shows anticarcinogenic activity. | [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. | [Synthesis]
A method for the preparation of α-carotene, the method of preparation comprising: a rearrangement reaction of diethyl 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,4-pentadienylphosphonate in an organic solvent under nitrogen protection, in th | [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.] | [References]
[1] R. WAY A W. Determination of α– and β–Carotene in Fruit and Vegetables by High Performance Liquid Chromatography[J]. Canadian Institute of Food Science and Technology journal, 1982, 16 1: 165-169. DOI: 10.1016/s0315-5463(82)72531-3
[2] M MURAKOSHI. Inhibitory effects of alpha-carotene on proliferation of the human neuroblastoma cell line GOTO.[J]. JNCI Journal of the National Cancer Institute, 1989, 81 21: 1649-1652. DOI: 10.1093/jnci/81.21.1649
[3] M MURAKOSHI. Potent preventive action of alpha-carotene against carcinogenesis: spontaneous liver carcinogenesis and promoting stage of lung and skin carcinogenesis in mice are suppressed more effectively by alpha-carotene than by beta-carotene.[J]. Cancer research, 1992, 52 23: 6583-6587.
[4] ANATOL KONTUSH. Lipophilic antioxidants in blood plasma as markers of atherosclerosis: the role of α-carotene and γ-tocopherol[J]. Atherosclerosis, 1999, 144 1: Pages 117-122. DOI: 10.1016/s0021-9150(99)00044-1
[5] ZHANG XUEHONG. Carotenoid intakes and risk of breast cancer defined by estrogen receptor and progesterone receptor status: a pooled analysis of 18 prospective cohort studies123[J]. American Journal of Clinical Nutrition, 2012, 95 3: Pages 713-725. DOI: 10.3945/ajcn.111.014415 |
|
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
|