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Details

Stereochemistry ACHIRAL
Molecular Formula C40H56
Molecular Weight 536.8726
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 11
Charge 0

SHOW SMILES / InChI
Structure of LYCOPENE

SMILES

CC(C)=CCC\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)CCC=C(C)C

InChI

InChIKey=OAIJSZIZWZSQBC-GYZMGTAESA-N
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+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf http://www.rxlist.com/lycopene-page2/supplements.htm

Lycopene is the fat-soluble pigment that gives tomatoes, watermelon, pink grapefruit, and other foods their red color. Bioavailability of lycopene is enhanced in the presence of lipids and thermal processing. Lycopene accounts for about 50% of the carotenoids found in human serum and is among the major carotenoids present in human milk. The antioxidant activity of lycopene and its use in cancer prevention and cardiovascular disease have been widely documented. The scientific literature documents some adverse reactions, such as diarrhea, dyspepsia, gas, nausea, and vomiting. One trial documented a cancer-related hemorrhage in a patient taking lycopene, although causality is unclear. Lycopene interacts with some cancer chemotherapy agents, as well as with ciprofloxacin and olestra.

CNS Activity

Curator's Comment: Lycopene was shown to cross the blood brain barrier and be present in the central nervous system in low concentrations. Deficiency of a series of anti-oxidation nutrients including lycopene is related to such neurodegenerative diseases as Parkinson’s disease, vascular dementia, Alzheimer disease, etc.

Originator

Sources: www.drugfuture.com/chemdata/lycopene.html
Curator's Comment: The molecular formula (C40H56) was established in 1910.

Approval Year

PubMed

PubMed

TitleDatePubMed
cis-trans isomers of lycopene and beta-carotene in human serum and tissues.
1992 Apr
Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene.
2000 Jan 1
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.
2000 Jan-Feb
Summary of safety studies conducted with synthetic lycopene.
2003 Apr
Noninvasive selective detection of lycopene and beta-carotene in human skin using Raman spectroscopy.
2004 Mar-Apr
Upregulation of connexin 43 by retinoids but not by non-provitamin A carotenoids requires RARs.
2005
Combination of S-allylcysteine and lycopene induces apoptosis by modulating Bcl-2, Bax, Bim and caspases during experimental gastric carcinogenesis.
2005 Aug
Protective effect of lycopene on adriamycin-induced cardiotoxicity and nephrotoxicity.
2006 Feb 1
Lycopene differentially induces quiescence and apoptosis in androgen-responsive and -independent prostate cancer cell lines.
2007 Apr
Gene expression profiling of aging in multiple mouse strains: identification of aging biomarkers and impact of dietary antioxidants.
2009 Aug
Lycopene: An antioxidant and radioprotector against gamma-radiation-induced cellular damages in cultured human lymphocytes.
2009 Jul 28
Differential effects of several phytochemicals and their derivatives on murine keratinocytes in vitro and in vivo: implications for skin cancer prevention.
2009 Jun
Dietary lycopene and tomato extract supplementations inhibit nonalcoholic steatohepatitis-promoted hepatocarcinogenesis in rats.
2010 Apr 15
Neurohepatic toxicity of subacute manganese chloride exposure and potential chemoprotective effects of lycopene.
2012 Jan
Inhibitory effects of lycopene on HMGB1-mediated pro-inflammatory responses in both cellular and animal models.
2012 Jun
Protection against chemotaxis in the anti-inflammatory effect of bioactives from tomato ketchup.
2014
Patents

Sample Use Guides

As a pure compound it has been studied in clinical trials at dosages of 13 to 75 mg/day. Dosage guidelines from manufacturers ranging from 10 to 30 mg taken twice daily with meals. For example, as an antioxidant, lycopene has been taken in doses of 6.5, 15, and 30 milligrams daily for eight weeks. To treat asthma caused by exercise, 30 milligrams of lycopene has been taken daily for one week.
Route of Administration: Oral
The lycopene showed significant antioxidant activity against nitric oxide radical with IC50 value of 57.879 ug/ml and antioxidant activity against reducing power method with IC50 value of 45.609 ug/ml respectively.
Name Type Language
LYCOPENE
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
INS-160D(III)
Code English
TOMAT-O-RED
Common Name English
TOMATO LYCOPENE [FHFI]
Common Name English
(ALL-TRANS)-LYCOPENE
Common Name English
LYCORED
Common Name English
LYCOPENE [MI]
Common Name English
LYCOPENE [MART.]
Common Name English
LYCOPENE PREPARATION [USP-RS]
Common Name English
LYCOPENE EXTRACT FROM TOMATO [FCC]
Common Name English
Solanorubin
Common Name English
(ALL-E)-2,6,10,14,19,23,27,31-OCTAMETHYL-2,6,8,10,12,14,16,18,20,22,24,26,30-DOTRIACONTATRIDECAENE
Common Name English
(ALL-E)-LYCOPENE (CONSTITUENT OF LYCOPENE AND TOMATO EXTRACT CONTAINING LYCOPENE) [DSC]
Common Name English
FEMA NO. 4110
Code English
CI 75125 [INCI]
Common Name English
LYCOPENE FROM BLAKESLEA TRISPORA [FCC]
Common Name English
NSC-407322
Code English
LYCOPENE [INCI]
Common Name English
BLAKESLEA TRISPORA
Common Name English
ATERONON
Brand Name English
REDIVIVO
Common Name English
Lycopene [WHO-DD]
Common Name English
LYCOPENE FROM BLAKESLEA TRISPORA
FCC  
Common Name English
E-160D(III)
Code English
(ALL-E)-LYCOPENE
Common Name English
INS NO.160D(III)
Code English
LYCOPENE EXTRACT FROM TOMATO
FCC  
Common Name English
MEXORYL SAQ
Common Name English
LYCOPENE [VANDF]
Common Name English
AEC LYCOPENE
Brand Name English
CI 75125
INCI  
INCI  
Official Name English
Classification Tree Code System Code
JECFA EVALUATION INS-160D(III)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
DSLD 164 (Number of products:1777)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
LOINC 27075-1
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
DSLD 1297 (Number of products:1)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
CODEX ALIMENTARIUS (GSFA) INS-160D(III)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
NCI_THESAURUS C68307
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
Code System Code Type Description
FDA UNII
SB0N2N0WV6
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
CHEBI
15948
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-949-1
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
WIKIPEDIA
LYCOPENE
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
PUBCHEM
446925
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
SMS_ID
100000088233
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PRIMARY
DAILYMED
SB0N2N0WV6
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
CAS
502-65-8
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
NSC
407322
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
NCI_THESAURUS
C2226
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
RS_ITEM_NUM
1370881
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PRIMARY
MESH
C015329
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
DRUG CENTRAL
4617
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID2046593
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
EVMPD
SUB21639
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
DRUG BANK
DB11231
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
MERCK INDEX
m6951
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY Merck Index
RXCUI
29008
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY RxNorm