103956-99-6

Basic information

• Product Name: (5Z)-12'-Apo-ψ-carotin-12'-al
• CAS NO: 103956-99-6
• Molecular Weight: 350.544
• Mol File: 103956-99-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (5Z)-12'-Apo-ψ-carotin-12'-al(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z)-12'-Apo-ψ-carotin-12'-al(103956-99-6)
• EPA Substance Registry System: (5Z)-12'-Apo-ψ-carotin-12'-al(103956-99-6)

Safety Data

• Hazardous Substances Data: 103956-99-6(Hazardous Substances Data)

Upstream product

• 502-65-8 lycopene 
• 103793-04-0 (2E,4E,6E)-8-Diaethoxyphosphoryl-3,7-dimethyl-2,4,6-octatriensaeure-methylester 
• 72612-84-1 (2E,4E,6E)-7-Formyl-3-methyl-2,4,6-octatriensaeure-methylester 
• 538315-01-4 (2E,4E,6E)-8-Hydroxy-3,7-dimethyl-2,4,6-octatriensaeure-methylester 
• 123556-68-3 (2E,4E,6E)-8-Bromo-3,7-dimethyl-octa-2,4,6-trienoic acid methyl ester 
• 103834-54-4 (all-E)-15-Apo-ψ-carotin-15-saeure-methylester 
• 19945-56-3 methyl 4-diethylphosphono-3-methyl-2-butenoate 
• 1070-48-0 (2E,4E,6E,8E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,8,10,14-hexadienal 
• 51575-60-1 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-2-butenal 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 131801-83-7 [3,7,11-trimethyl-dodecyl-2,4,6,10-tetraenyl]-triphenylphosphonium chloride 
• 59060-56-9 triphenyl-((2E,4E,6E)-3,7,11-trimethyl-dodeca-2,4,6,10-tetraenyl)-phosphonium; bromide 
• 59121-99-2 (4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraene-3-ol 
• 145571-82-0 (all-E)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol 

Downstream Products

• 502-64-7 all-trans-neurosporene 
• 472-93-5 trans-gamma-Carotene 

Relevant articles and documents

10'-Apolycopin-10'-ol und 10'-Apolycopin-10'-saeure aus Blueten der Rosenhybride "Marechal Niel"

The novel 10'-apolycopen-10'-ol (1) and 10'-oic acid (4) were isolated from the yellow petals of the once world-renowned rose hybrid "Marechal Niel".The relative amount of either 1 or 4 produced by the plant depends upon the climatic conditions.Both 1 and

Identification and quantification of apo-lycopenals in fruits, vegetables, and human plasma

Research has suggested that lycopene may be metabolized by eccentric cleavage, catalyzed by β-carotene oxygenase 2, resulting in the generation of apo-lycopenals. Apo-6′-lycopenal and apo8′-lycopenal have been reported previously in raw tomato. We now show that several other apolycopenals are also present in raw and processed foods, as well as in human plasma. Apo-lycopenal standards were prepared by in vitro oxidation of lycopene, and a high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method using atmospheric pressure chemical ionization in negative mode was developed to separate and detect the apo-6′-, apo-8′-, apo-10′-, apo-12′-, apo-14′-, and apo-15′-lycopenal products formed in the reaction. Hexane/acetone extracts of raw tomato, red grapefruit, watermelon, and processed tomato products were analyzed, as well as plasma of individuals who had consumed tomato juice for 8 weeks. Apo-6′-, apo-8′-, apo-10′-, apo-12′-, and apo-14′-lycopenals were detected and quantified in all food products tested, as well as plasma. The sum of apo-lycopenals was 6.5 μg/100 g Roma tomato, 73.4μg/100 g tomato paste, and 1.9 nmol/L plasma. We conclude that several apo-lycopenals, in addition to apo-6′- and -8′-lycopenal, are present in lycopene-containing foods. In addition, the presence of apo-lycopenals in plasma may derive from the absorption of apo-lycopenals directly from food and/or human metabolism.

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).