Carotene Chemical Properties

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 

Solid

color 

Orange to Very Dark Orange

Odor

Slight characteristic

optical activity

〔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|

Safety Information

Hazard Codes 

Xn

Risk Statements 

40-67-36/37/38

Safety Statements 

36/37-24/25-23

RIDADR 

UN 1593 6.1/PG 3

WGK Germany 

3

HS Code 

32041990

MSDS

• Language:English Provider:R(+)-alpha-Carotene

Carotene Usage And Synthesis

Description

α-Carotene is a precursor of vitamin A that has been found in various fruits and vegetables. It inhibits proliferation of GOTO human neuroblastoma cells more potently than β-carotene and halts the cell cycle at the G₀/G₁ phase concomitantly with a reduction in 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%. α-Carotene levels are increased in patients with coronary heart disease and are inversely correlated with the risk of estrogen receptor-negative breast cancer.

Uses

carotene is used to provide a red-orange color in cosmetic formulations. It is the primary yellow coloring component of butter, carrots, and egg yolk. Carotene is found in plants as well as in many animal tissues.

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.

Uses

(6''R)-β,ε-Carotene is a trans isomer of carotenoid pigment found in plants. It is a terpenoid hydrocarbon.

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.

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

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