472-93-5

Basic information

• Product Name: γ-Carotene
• Synonyms: GAMMACAROTENE;g-Carotene
• CAS NO: 472-93-5
• Molecular Formula: C₄₀H₅₆
• Molecular Weight: 536.87264
• Mol File: 472-93-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 152-153.5°; mp 177.5°
• Boiling Point: 644.94°C (rough estimate)
• Flash Point: 348.4°C
• Appearance: /
• Density: 0.9380 (estimate)
• Vapor Pressure: 1.89E-16mmHg at 25°C
• Refractive Index: 1.5630 (estimate)
• Storage Temp.: -20°C
• BRN: 3226412
• CAS DataBase Reference: γ-Carotene(CAS DataBase Reference)
• NIST Chemistry Reference: γ-Carotene(472-93-5)
• EPA Substance Registry System: γ-Carotene(472-93-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 472-93-5(Hazardous Substances Data)

Usage

Uses

γ-Carotene may be used as a reference standard in the determination of γ-carotene in fruits using high performance liquid chromatography coupled with diode array detector (HPLC-DAD) and mass spectrometry (HPLC-MS).

Definition

ChEBI: A cyclic carotene obtained by the cyclisation of lycopene.

General Description

γ-Carotene is a plant carotenoid with provitamin A activity.

Biochem/physiol Actions

Metabolite in carotenoid biosynthesis and the biosynthesis of plant secondary metabolites.

Purification Methods

Purify γ-carotene by chromatography on alumina [Grade II in pet ether (b 60-80o) and elute with *C6H6], or magnesia columns. When crystallised from *C6H6/MeOH (2:1), it had m 177.5o. Store it in the dark, under an inert atmosphere at 0o, or in an evacuated tube at -20o. The purity is verified by TLC on Ca(OH)2/Kieselgel (8:2) using pet ether (b 60-80o) as eluant. [Manchand et al. J Chem Soc 2019 1965, Beilstein 5 III 2453, 5 IV 2617.]

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

Upstream product

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Downstream Products

• 13879-21-5 β,ψ-caroten-4-one 
• 36210-86-3 (+/-)-β,ψ-caroten-4-ol 

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.

Synthesen von Carotinen mit ψ-Endgruppen und (Z)-Konfiguration an terminalen konjugierten Doppelbindungen

Five carotenes bearing (5Z)-ψ-end groups were synthesized and carefully characterized: (5Z)-lycopene (6), (5Z,5'Z)-lycopene (7), (5'Z)-neurosporene (8), (5'Z)-β,ψ-carotene (12), and (5'Z)-εψ-carotene (14).