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SMB00706

Sigma-Aldrich

Lycopene

≥98% (HPLC), from tomato

Synonym(s):

ψ,ψ-Carotene, 2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene

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About This Item

Empirical Formula (Hill Notation):
C40H56
CAS Number:
Molecular Weight:
536.87
MDL number:
UNSPSC Code:
12352205
NACRES:
NA.28

biological source

tomato

Quality Level

assay

≥98% (HPLC)

form

powder

mol wt

536.87

storage condition

protect from light

solubility

THF: 1 mg/mL
chloroform: 5 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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, an acyclic carotenoid pigment, is a bioactive natural compound commonly produced by many red fruits and vegetables such as watermelon, pink guava, and tomato, and photosynthetic algae. Current research suggests that this plant metabolite acts as an inhibitor and may exhibit diverse biological activities, including antioxidant, anti-carcinogenic, radioprotective, anticancer and anti-inflammatory properties.

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

Lycopene is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and drug discovery research.

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.

Features and Benefits

  • High quality compound suitable for multiple research applications
  • Compatible with HPLC and mass spectrometry techniques

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Alireza Milani et al.
British journal of pharmacology, 174(11), 1290-1324 (2016-10-30)
Carotenoids and retinoids have several similar biological activities such as antioxidant properties, the inhibition of malignant tumour growth and the induction of apoptosis. Supplementation with carotenoids can affect cell growth and modulate gene expression and immune responses. Epidemiological studies have
Lycopene: potent antioxidant for oral premalignancy and oral cancer
Sonunu, S.; et al.
European Journal of Biomedical AND Pharmaceutical sciences, 2, 135-144 (2015)
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
Bo-Yi Jhou et al.
Journal of agricultural and food chemistry, 65(32), 6893-6903 (2017-07-21)
NADPH oxidase 4 (NOX4), with the sole function to produce reactive oxygen species (ROS), can be a molecular target for disrupting cancer metastasis. Several studies have indicated that lycopene exhibited anti-metastatic actions in vitro and in vivo. However, the role

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