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Structure Database (LMSD)

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Common Name

alpha-Carotene

Systematic Name

(6'R)-β,ε-Carotene

Synonyms

beta,epsilon-Carotene

LM ID

LMPR01070011

Formula

C₄₀H₅₆

Exact Mass

Calculate m/z

536.4382

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

α-Carotene is a precursor of vitamin A that has been found in various fruits and vegetables.¹ 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.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

This information has been provided by Cayman Chemical

References

1. Zhang, X., Spiegelman, D., Baglietto, L., et al. Carotenoid intakes and risk of breast cancer defined by estrogen receptor and progesterone receptor status: A pooled analysis of 18 prospective cohort studies. Am. J. Clin. Nutr. 95(3), 713-725 (2012).

2. Kontush, A., Spranger, T., Reich, A., et al. Lipophilic antioxidants in blood plasma as markers of atherosclerosis: The role of α-carotene and γ-tocopherol. Atherosclerosis 144(1), 117-122 (1999).

3. Murakoshi, M., Nishino, H., Satomi, Y., et al. Potent preventive action of α-carotene against carcinogenesis: spontaneous liver carcinogenesis and promoting stage of lung and skin carcinogenesis in mice are suppressed more effectively by α-carotene than by β-carotene. Cancer Res. 52(23), 6583-6587 (1992).

4. Murakoshi, M., Takayusa, J., Kimura, O., et al. Inhibitory effects of α-carotene on proliferation of the human neuroblastoma cell line GOTO. J. Natl. Cancer Inst. 81(21), 1649-1652 (1989).

5. Bushway, R.J., and Wilson, A.M. Determination of α- and β-carotene in fruit and vegetables by high performance liquid chromatography. Can. Inst. Food Sci. Technol. J. 15(3), 165-169 (1982).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Polysiphonia urceolata (#65404)

Florideophyceae (#2806)

Carotenoids in red algae,
Phytochemistry, 1976

DOI: 10.1016/S0031-9422(00)89006-8

Homo sapiens (#9606)

Mammalia (#40674)

Major Carotenoids in Mature human Milk: Longitudinal and Diurnal Patterns,
J Hutr Biochem, 1998

DOI: 10.1016/S0955-2863(97)00132-0

String Representations

InChiKey (Click to copy)

ANVAOWXLWRTKGA-NTXLUARGSA-N

InChi (Click to copy)

InChI=1S/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

SMILES (Click to copy)

C1C(C)(C)C(/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(C)=CCCC2(C)C)=C(C)CC1