Apocarotenal

Base Information

• Chemical Name: Apocarotenal
• CAS No.: 1107-26-2
• Deprecated CAS: 2756-57-2,4172-46-7
• Molecular Formula: C30H40 O
• Molecular Weight: 416.647
• Hs Code.: 3204196000
• European Community (EC) Number: 214-171-6,235-767-2
• NSC Number: 374897
• UNII: V22N3E2U32
• DSSTox Substance ID: DTXSID20883251
• Nikkaji Number: J1.244.239D,J1.882.183D,J14.370G
• Wikipedia: Apocarotenal
• Wikidata: Q274972
• Metabolomics Workbench ID: 58567
• Mol file: 1107-26-2.mol

Synonyms:apocarotenal

Chemical Property of Apocarotenal

Chemical Property:

• Melting Point: 138-141 °C
• Boiling Point: 575.7°Cat760mmHg
• Flash Point: 273.8°C
• PSA: 17.07000
• Density: 0.949g/cm³
• LogP: 8.72190
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 1 mg/mL, clear to very faintly turbid, intense
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 416.307915895
• Heavy Atom Count: 31
• Complexity: 887

Purity/Quality:

98%,99%, ^*data from raw suppliers

Apocarotenal United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=O)/C)/C
• Description: trans-β-Apo-8′-carotenal is a dark purple crystal or crystalline fine powder with metallic luster. It is one of the oxidation products of carotenoids contained in citrus. It is insoluble in water and can be dispersed in hot water. It is easily soluble in chloroform, insoluble in ethanol, and slightly soluble in vegetable oil and acetone. Industrial products soluble in oils or organic solvents, with stable performance.
• Uses: β-apo-8 -carotenal is used to color juices, fruit drinks, soups, jams, jellies, and gelatin. β-Apo-8'-carotenal is an antioxidant β-carotene (C184250) derivative found in Cucumis melo melons and traditional Portuguese fruits and vegetables. Studies have shown that β-Apo-8'-carotenal decreased the in vivo AFB1-induced DNA SSB and the binding of AFB1 to liver DNA and increased in vitro AFB1 metabolism to aflatoxin M1, a less genotoxic metabolite. Beta-Apo-8'-Carotenal is a colorant that is a carotenoid producing a light to dark orange hue. It has fair light stability, poor oxidation stability, and good ph stability. It is insoluble in water but is available in water-dispersible, oil-dispersible, and oil-soluble forms. It has vitamin a activity. It is used in cheese and cheese sauces, and dressings. The maximum usage level is 33 ppm. Related colorants are beta-carotene and canthaxanthin.

Technology Process of Apocarotenal

There total 20 articles about Apocarotenal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

crocetindial (502-70-5) + C28H32ClP → trans-β-apo-8'-carotenal (1107-26-2,4172-46-7)

Guidance literature:

C₂₈H₃₂ClP; With sodium methylate; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

crocetindial; In methanol; at 20 ℃; for 4h; Time; Inert atmosphere;

Reference yield:

beta-carotene (7235-40-7) → (E)-β-ionone (79-77-6,14901-07-6) + 4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptaenal (640-49-3) + 2,6,6-trimethylcyclohex-1-enecarbaldehyde (432-25-7) + trans-β-apo-8'-carotenal (1107-26-2,4172-46-7) + 5,6-epoxy-trans-β-ionone (36340-49-5)

Guidance literature:

With tert.-butylhydroperoxide; μ-carbido-bis[(5,10,15,20-tetraphenyl-21H,23H-porphyrinato)iron(IV)]; In benzene; at 24.84 ℃; Reagent/catalyst; Kinetics;

DOI:10.1134/S0036024418110390

Reference yield:

all-trans-β-apo-8'-Carotenol (6541-41-9) → trans-β-apo-8'-carotenal (1107-26-2,4172-46-7)

Guidance literature:

With manganese(IV) oxide; In 1,2-dichloro-ethane; at 25 - 30 ℃; for 10h; Solvent; Temperature; Inert atmosphere;

upstream raw materials:

beta-carotene

15-cis-8'-apo-β-caroten-8'-al

(2E,4E,6E)-8,8-dimethoxy-3,7-dimethyl-octa-2,4,6-trienal

Retinyltriphenylphosphonium Chloride

Downstream raw materials:

trans-β-apo-8'-carotenal

4-hydroxy-8'-apo-β-carotin-8'-al

15-cis-8'-apo-β-caroten-8'-al

9-cis β-apo-8'-carotenal

Refernces

• 1、 Edge, Ruth,Land, Edward J.,McGarvey, David,Mulroy, Louise,Truscott, T. George. "Relative one-electron reduction potentials of carotenoid radical cations and the interactions of carotenoids with the vitamin E radical cation". . p. 4087 - 4090. Retrieved 1998.
• 2、 Simonova,Zaitseva,Tyulyaeva, E. Yu.,Zdanovich,Koifman. "Kinetics of β-Carotene Oxidation in the Presence of Highly Active Forms of μ-Carbido Diiron(IV) Tetraphenylporphyrinate". . p. 2128 - 2134. Retrieved 2018.
• 3、 -. "Preparation method of beta-apo-8 '-carotene aldehyde". Paragraph 0035; 0039-0042; 0043; 0045-0046; 0049; 0053-0054. . Retrieved 2021/02/24.