Merck
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L9879

Sigma-Aldrich

Lycopene

≥90%, 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
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

biological source

tomato

assay

≥90%

form

powder

shipped in

dry ice

storage temp.

−70°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 naturally occurring red pigment, which belongs to the family of carotenoids. It is found in tomatoes, watermelon and papaya. Lycopene has antioxidant property.

Application

Lycopene has been used:
  • in high performance liquid chromatography (HPLC) to determine its concentration in liver, kidney and lung tissue
  • to induce urokinase plasminogen activator receptor (uPAR) IN prostate cancer cell line
  • in Raman chemical imaging system to detect and visualize its internal distribution

Packaging

1, 5, 10 mg in ampule
sealed ampule

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L9879.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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Articles

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. LDL receptors regulate the cellular transport of lipid rich low density lipoprotein (LDL) particles.

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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