640-49-3

Basic information

• Product Name: β-Apocarotenal
• Synonyms: (2E,4E,6E,8E,10E,12E,14E)-15-(2,6,6-Trimethyl-1-cyclohexenyl)-4,9,13-trimethyl-2,4,6,8,10,12,14-pentadecaheptaenal;10'-Apo-β,β-caroten-10'-al;10'-Apo-β,ψ-caroten-10'-al;β-Apo-10'-carotenal
• CAS NO: 640-49-3
• Molecular Formula: C₂₇H₃₆O
• Molecular Weight: 376.57
• Mol File: 640-49-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 534.6°C at 760 mmHg
• Flash Point: 258.4°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 1.67E-11mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: β-Apocarotenal(CAS DataBase Reference)
• NIST Chemistry Reference: β-Apocarotenal(640-49-3)
• EPA Substance Registry System: β-Apocarotenal(640-49-3)

Safety Data

• Hazardous Substances Data: 640-49-3(Hazardous Substances Data)

Usage

Uses

10’-Apo-β-carotenal is an antioxidant β-carotene (C184250) derivative that facilitates embryogenesis as a substrate for BCO1-catalyzed retinoid formation.

Definition

ChEBI: An apo carotenoid compound arising from oxidative degradation of the beta,beta-carotene skeleton at the 10'-position.

InChI:InChI=1/C27H36O/c1-22(12-7-8-13-23(2)16-11-21-28)14-9-15-24(3)18-19-26-25(4)17-10-20-27(26,5)6/h7-9,11-16,18-19,21H,10,17,20H2,1-6H3/b8-7+,14-9+,16-11+,19-18+,22-12+,23-13+,24-15+

Upstream product

• 16910-83-1 15,15'-didehydro-10'-apo-β-caroten-10'-al 
• 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 
• 7235-40-7 beta-carotene 
• 69774-12-5 methyl (2E,4E,6E,8E,10E,12E,14E)-4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-en-1-yl)pentadeca-2,4,6,8,10,12,14-heptaenoate 
• 432552-01-7 4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptanoic acid ethyl ester 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 
• 1638-05-7 12'-apo-β-caroten-12'-al 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 6541-42-0 (2E,4E,6E,8E,10E,12E,14E)-4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-en-1-yl)pentadeca-2,4,6,8,10,12,14-heptaen-1-ol 
• 161023-01-4 β-carotene 

Downstream Products

• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 432552-03-9 C₃₂H₄₃⁽³⁾HO₂ 
• 432552-02-8 C₂₇H₃₅⁽³⁾HO 

Relevant articles and documents

Synthetic method of beta-apo-8'-carotenoic ethyl ester

The invention relates to the technical field of feed additives, and discloses a synthesis method of beta-apo-8'-carotenoic ethyl ester. According to the invention, beta-apo-8'-carotenoic ethyl ester is synthesized through a route of C10 + C2-> C12, C12 + C15-> C27, and C27 + C3-> C30, wherein in the route, C10 dialdehyde, vinyl ether (R is alkyl), C15 triphenyl phosphonium salt (X is Br or Cl) and ethoxyformyl ethylidene triphenylphosphine which are used as reactants are rich in source and low in cost, Vitamin A with high raw material cost does not need to be used, purification steps in the synthesis process are few, and operation is simple, so that the synthesis route is low in industrialization difficulty, large-scale production is easy to achieve, and the production cost of the beta-apo-8'-carotenoic ethyl ester is reduced.

Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases

A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.

A Supramolecular Enzyme Mimic That Catalyzes the 15,15′ Double Bond Scission of β,β-Carotene

-