1638-05-7

Basic information

• Product Name: 12APOBETACAROTENAL
• Synonyms: 12APOBETACAROTENAL;12′-Apo-beta, psi-carotenal;2,7,11-trimethyl-13-(2,6,6-trimethylcyclohex-1-en-1-yl)tridecahexaen-2,4,6,8,10,12-al;(2E,4E,6E,8E,10E,12E)-13-(2,6,6-Trimethyl-1-cyclohexenyl)-2,7,11-trimethyl-2,4,6,8,10,12-tridecahexaenal;12'-Apo-β,β-caroten-12'-al;12'-Apo-β,ψ-caroten-12'-one;β-Apo-12'-carotenal
• CAS NO: 1638-05-7
• Molecular Formula: C₂₅H₃₄O
• Molecular Weight: 350.53686
• EINECS: 415-770-7
• Mol File: 1638-05-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 88-89 °C
• Boiling Point: 503.143°C at 760 mmHg
• Flash Point: 243.777°C
• Appearance: /
• Density: 0.949g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 12APOBETACAROTENAL(CAS DataBase Reference)
• NIST Chemistry Reference: 12APOBETACAROTENAL(1638-05-7)
• EPA Substance Registry System: 12APOBETACAROTENAL(1638-05-7)

Safety Data

• Hazard Codes: Xn
• Statements: 43-48/22-52/53
• Safety Statements: 22-36/37-61
• Hazardous Substances Data: 1638-05-7(Hazardous Substances Data)

Usage

Uses

12''-Apo-β,ψ-carotenal is an anti-oxidant molecule from gum arabic and maltodextrin microcapsules; Also, it is used as an ultrafast probe for ionic liquids.

InChI:InChI=1/C25H34O/c1-20(11-7-8-12-22(3)19-26)13-9-14-21(2)16-17-24-23(4)15-10-18-25(24,5)6/h7-9,11-14,16-17,19H,10,15,18H2,1-6H3/b8-7+,13-9+,17-16+,20-11+,21-14+,22-12+

Upstream product

• 7235-40-7 beta-carotene 
• 79-77-6 (E)-β-ionone 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 16910-82-0 15,15'-didehydro-12'-apo-β-caroten-12'-al 
• 5056-17-7 2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde 
• 186194-14-9 diethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonate 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 129975-66-2 ((2E,4E)-5-[1,3]Dioxolan-2-yl-4-methyl-penta-2,4-dienyl)-phosphonic acid diethyl ester 
• 129975-63-9 ((E)-3-[1,3]Dioxolan-2-yl-2-methyl-allyl)-phosphonic acid diethyl ester 
• 209615-09-8 2,2'-(1,6-Dimethyl-1,3,5-hexatrienylen)bis(5,5-dimethyl-1,3-dioxan) 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 
• 1107-26-2 trans-β-apo-8'-carotenal 
• 116-31-4 all-trans-Retinal 
• 146918-87-8 ((E)-3-[1,3]Dioxolan-2-yl-but-2-enyl)-phosphonic acid diethyl ester 

Downstream Products

• 95343-58-1 9-cis-7,8-didehydro-5,6-dihydro-β,β-carotene-3,6-diol 
• 72843-12-0 (3S)-Hydroxyechinenon 
• 4339-77-9 3-hydroxy-β,β-caroten-4-one 
• 1050-75-5 (2E,4E,6E,8E,10E,12E)-2,7,11-trimethyl-13-(2,6,6-trimethylcyclohex-1-en-1-yl)trideca-2,4,6,8,10,12-hexaene-1-ol 
• 514-90-9 7',8'-dihydro-β,ψ-carotene 
• 17092-92-1 (7aR)-5,6,7,7a-tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone 
• 79-77-6 (E)-β-ionone 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 36340-49-5 5,6-epoxy-trans-β-ionone 
• 65861-49-6 4-oxo-β-apo-12’-carotenal 

Relevant articles and documents

Isolation by high-pressure liquid chromatography of cis-trans isomers of β-apo-12'-carotenal and determination of their configurations by 1H NMR spectroscopy

High pressure liquid chromatography of an isomeric mixture of β-apo-12'-carotenal, which was obtained by iodine-sensitized photo-isomerization, resolved eleven peaks of cis-trans isomers.The configurations of eight isomers, i.e., all-trans, 9-, 13-, 15-, 13'-mono-cis, and 9,13-, 9,13'- and 13,13'-di-cis, were determined by 1H NMR spectroscopy. 1H,1H COSY and long-range 1H,1H COSY spectra was used for the assignments of all the 1H signals.The isomerization shifts of the olefinic 1H signals and the NOE correlations, which were idenfied in the 1H,1H NOESY spectra, were used for the configurational determinations.In relation to the difference in isomeric composition between retinoids and carotenoids, the cis configurations found in the present compound (C25 aldehyde) are compared with those found in retinal (C20 aldehyde) and β-apo-8'-carotenal (C30 aldehyde) having a shorter and a longer conjugated chain, respectively.

Use of insoluble polymer supports in organic synthesis. 9. Synthesis of unsymmetrical carotenoids on solid phases.

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Synthesis of all-trans-[10′-3H]-8′-apo-β-carotenoic acid

The enzyme, 15, 15′-β-carotene dioxygenase (BCDOX), facilitates the oxidation of β-carotene to yield retinal. This is a remarkable process in which one of 11 double bonds in β-carotene is selectively oxidized. To further probe the mechanistic aspects of BCDOX, the synthesis of all-trans-[10′-3H]-8′-apo-β-carotenoic acid is reported. This compound will be used as a photoaffinity labeling reagent to probe the β-carotene binding pocket within BCDOX. The synthesis outlines a simple and efficient route for the incorporation of tritium at the 10′ olefinic carbon of 8′-apo-β-carotenoic acid. Copyright