64727-64-6

Basic information

• Product Name: 9-CIS-LYCOPENE
• Synonyms: 9-CIS-LYCOPENE
• CAS NO: 64727-64-6
• Molecular Formula: C₄₀H₅₆
• Molecular Weight: 536.87264
• Mol File: 64727-64-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 660.9°C at 760 mmHg
• Flash Point: 350.7°C
• Appearance: /
• Density: 0.888g/cm³
• Vapor Pressure: 1.33E-16mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 9-CIS-LYCOPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-CIS-LYCOPENE(64727-64-6)
• EPA Substance Registry System: 9-CIS-LYCOPENE(64727-64-6)

Safety Data

• Hazardous Substances Data: 64727-64-6(Hazardous Substances Data)

Usage

InChI:InChI=1/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+

Upstream product

• 2361-24-2 7,9,9',7'-tetra-cis-lycopene 
• 1116695-27-2 9,24-dibromo-8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaene 
• 1116695-26-1 8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(1-ethoxyethyl) ether 
• 1116695-25-0 8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(tetrahydropyranyl) ether 
• 1116695-24-9 8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(methoxymethyl) ether 
• 359643-76-8 7,7',11,11'-tetra(phenylsulfonyl)-7,7',8,8',11,11',12,12'-octahydrolycopene 
• 58689-15-9 pseudoionone 
• 103793-14-2 [(2E,6E)-8-(Diethoxy-phosphoryl)-2,7-dimethyl-octa-2,6-dien-4-ynyl]-phosphonic acid diethyl ester 
• 13018-46-7 (13Z)-lycophene 
• 101468-86-4 7-cis-lycopene 
• 20082-23-9 (4E,6E/Z)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol 
• 1071-89-2 (4E,6E/Z)-3,7,11-Trimethyldodeca-1,4,6,10-tetraen-3-ol 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 145571-84-2 Triphenyl<(2E,4E,6Z)-3,7,11-trimethyldodeca-2,4,6,10-tetraenyl>phosphonium Bromide 

Downstream Products

• 13018-46-7 (13Z)-lycophene 
• 502-65-8 lycopene 
• 101468-86-4 7-cis-lycopene 
• 162990-51-4 C₄₀H₅₆ 
• 4418-71-7 lycopene 

Relevant articles and documents

Plant carotene cis-trans isomerase CRTISO: A new member of the FAD red-dependent flavoproteins catalyzing non-redox reactions

The carotene cis-trans isomerase CRTISO is a constituent of the carotene desaturation pathway as evolved in cyanobacteria and prevailing in plants, in which a tetra-cis-lycopene species, termed prolycopene, is formed. CRTISO, an evolutionary descendant of the bacterial carotene desaturase CRTI, catalyzes the cis-to-trans isomerization reactions leading to all-trans-lycopene, the substrate for the subsequent lycopene cyclization to form all-trans-α/ β-carotene. CRTISO and CRTI share a dinucleotide binding motif at the N terminus. Here we report that this site is occupied by FAD in CRTISO. The reduced form of this cofactor catalyzes a reaction not involving net redox changes. Results obtained with C(1)- and C(5)-deaza-FAD suggest mechanistic similarities with type II isopentenyl diphosphate: dimethylallyl diphosphate isomerase (IDI-2). CRTISO, together with lycopene cyclase CRTY and IDI-2, thus represents the third enzyme in isoprenoid metabolism belonging to the class of non-redox enzymes depending on reduced flavin for activity. The regional specificity and the kinetics of the isomerization reaction were investigated in vitro using purified enzyme and biphasic liposome-based systems carrying specific cis-configured lycopene species as substrates.Thereaction proceeded from cis to trans, recognizing half-sides of the symmetrical prolycopene and was accompanied by one trans-to-cis isomerization step specific for the C(5)-C(6) double bond. Rice lycopene β-cyclase (OsLCY-b), when additionally introduced into the biphasic in vitro system used, was found to be stereospecific for all-trans-lycopene and allowed the CRTISO reaction to proceed toward completion by modifying the thermodynamics of the overall reaction.

Stable and bioavailable compositions of isomers of carotenoids for skin and hair

The present invention relates to a method of manufacturing a stable composition enriched in cis-lycopene (z-isomers) by prolonged heating in solvents of tomatoes, parts of tomatoes, derivative thereof or tomato extracts in solvents.

Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes

Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS-spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5'Z)-, (7Z,7'Z)-, (7Z,9Z)-, (9Z,9'Z)-, and (7Z,9Z,7'Z,9'Z)-lycopene.Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9'Z)-, (9Z,13'Z)-, (5Z,9Z,5'Z)-, and (5Z,13Z,5'Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep.HPLC and were identified by 1H-NMR spectroscopy.