SMB00706

Sigma-Aldrich

Lycopene

≥98% (HPLC), from tomato

Synonym(s):
2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene, ψ,ψ-Carotene
Empirical Formula (Hill Notation):
C40H56
CAS Number:
Molecular Weight:
536.87
MDL number:

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

solubility

THF: 1 mg/mL
chloroform: 5 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

C\C(C)=C\CC\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=C(/C)CC\C=C(\C)C

InChI

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

InChI key

OAIJSZIZWZSQBC-GYZMGTAESA-N

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General description

Lycopene is a carotenoid found in many red fruits and vegetables such as watermelon, pink guava, and tomato. Lycopene is a potent antioxidant. It is suggested that lycopene is used by the plant to protect against reactive oxygen species (ROS).

Application

Lycopene has been used:
  • to analyze its chemo-preventive effects on cutaneous tumors in in vitro mouse epidermal cell line
  • as a reference standard for quantitative high-performance liquid chromatography (HPLC) to analyze antioxidant capacity of endogenous carotenoids in mammalian cell lines
  • as a reference standard in high-performance liquid chromatography (HPLC) to identify carotenoids from engineered Saccharomyces cerevisiae

Biochem/physiol Actions

Antioxidant micronutrient of tomatoes associated with decreased risk for cancer and cardiovascular disease. Enhances gap juction communication between cells via upregulation of connexin 43 and reduces proliferation of cancer cells in culture. Inhibits cholesterol synthesis and enhances low-density lipoprotein degradation.
Lycopene has been found to be active against oral cancer and to inhibit metastasis of human liver adenocarcinoma cells by down regulation of NOX4. Lycopene was also found to be a beneficial supplement for people with cardiovascular diseases.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

High-level beta-carotene production from xylose by engineered Saccharomyces cerevisiae without overexpression of a truncated HMG1 (tHMG1)
Sun L, et al.,
Biotechnology and Bioengineering, 3522-3532 (2020)
Sonia Gupta et al.
International journal of preventive medicine, 6, 70-70 (2015-09-04)
Without pigments, we are nothing. Life presents us with a kaleidoscope of colors. From the green grass of home to a forest's ruddy autumn hues, we are surrounded by living colors. Living things obtain their colors, with few exceptions, from...
Subramaniam Pennathur et al.
Free radical biology & medicine, 49(2), 205-213 (2010-04-15)
Lycopene, a carotenoid found in tomatoes, is a proven antioxidant that may lower the risk of certain disorders including heart disease and cancer. Hypochlorous acid (HOCl) is an oxidant linked to tissue oxidation in cardiovascular disease and other inflammatory disorders...
Lycopene: potent antioxidant for oral premalignancy and oral cancer
Sonunu, S.; et al.
European Journal of Biomedical AND Pharmaceutical sciences, 2, 135-144 (2015)
A V Rao et al.
Journal of the American College of Nutrition, 19(5), 563-569 (2000-10-07)
Lycopene, a carotenoid without provitamin-A activity, is present in many fruits and vegetables; however, tomatoes and processed tomato products constitute the major source of lycopene in North American diet. Among the carotenoids, lycopene is a major component found in the...

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