9-cis-beta-Carotene

Base Information

• Chemical Name: 9-cis-beta-Carotene
• CAS No.: 13312-52-2
• Molecular Formula: C40H56
• Molecular Weight: 536.885
• UNII: 3K5NFW97PV
• DSSTox Substance ID: DTXSID70920483
• Nikkaji Number: J426.849K
• Wikidata: Q27135678
• Metabolomics Workbench ID: 64971
• Mol file: 13312-52-2.mol

Synonyms:9-cis-beta-carotene;13312-52-2;9-cis-|A-Carotene;9-Cis-beta,beta-Carotene;(9Z)-beta-Carotene;beta-Carotene, (9Z)-;beta,beta-Carotene, neo-U;beta,beta-Carotene, 9-cis-;UNII-3K5NFW97PV;3K5NFW97PV;CHEBI:67188;1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15Z,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene;neo-beta-carotene U;9-Cis Beta-Carotene;9-cis-??-Carotene;NEO-.BETA.-CAROTENE U;9-CIS-.BETA.-CAROTENE;(9Z)-.BETA.-CAROTENE;DTXSID70920483;OENHQHLEOONYIE-BVZAMQQESA-N;.BETA.-CAROTENE, NEO U-;.BETA.-CAROTENE, (9Z)-;AKOS040740678;(9Z)-.BETA.,.BETA.-CAROTENE;9-CIS-.BETA.,.BETA.-CAROTENE;(9CIS)-.BETA.,.BETA.-CAROTENE;LS-96057;.BETA.,.BETA.-CAROTENE, 9-CIS-;HY-136234;(9Z)-beta-Carotene, >=90.0% (HPLC);CS-0120904;C20484;Q27135678;2,2'-((1E,3Z,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-TETRAMETHYLOCTADECA-1,3,5,7,9,11,13,15,17-NONAENE-1,18-DIYL)BIS(1,3,3-TRIMETHYLCYCLOHEX-1-ENE)

Chemical Property of 9-cis-beta-Carotene

Chemical Property:

• Boiling Point: 654.7±22.0 °C(Predicted)
• PSA: 0.00000
• Density: 0.941±0.06 g/cm3(Predicted)
• LogP: 12.60580
• Storage Temp.: ?20°C
• XLogP3: 13.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 10
• Exact Mass: 536.438201786
• Heavy Atom Count: 40
• Complexity: 1120

Purity/Quality:

99%, ^*data from raw suppliers

(9Z)-β-Carotene ≥90.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(CCCC2(C)C)C)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=C\C2=C(CCCC2(C)C)C)/C)/C
• Uses: The 9-cis isomer of β-Caroten (C184250). Carrots are one of the highest dietary sources of β-carotene and are naturally high in the (all-E)-β-carotene isomer, which has higher bioavailability, provitamin A activity, and antioxidant capacity compared to Z (cis) isomers.

Technology Process of 9-cis-beta-Carotene

There total 62 articles about 9-cis-beta-Carotene 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: 63.0%

all-trans-Retinal (116-31-4) + C38H44P(1+)*Br(1-) → 9-cis-β-carotene (13312-52-2)

Guidance literature:

C₃₈H₄₄P⁽¹⁺⁾*Br^(1-); With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

all-trans-Retinal; In tetrahydrofuran; at -78 - 25 ℃; for 1.5h;

Reference yield: 60.0%

(2-(1E,3Z)-4-iodo-3-methylbuta-1,3-dien-1-yl)-1,3,3-trimethylcyclohex-1-ene + C35H48Si → 9-cis-β-carotene (13312-52-2)

Guidance literature:

C₃₅H₄₈Si; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

(2-(1E,3Z)-4-iodo-3-methylbuta-1,3-dien-1-yl)-1,3,3-trimethylcyclohex-1-ene; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 25 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/chem.201903080

Reference yield: 32.0%

(2-(1E,3Z)-4-iodo-3-methylbuta-1,3-dien-1-yl)-1,3,3-trimethylcyclohex-1-ene + C23H34OSi2 + 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene (138846-06-7) → 9-cis-β-carotene (13312-52-2)

Guidance literature:

C₂₃H₃₄OSi₂; With potassium trimethylsilonate; In tetrahydrofuran; 1,4-dioxane; at 25 ℃; for 0.25h; Inert atmosphere;

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene; With bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; at 25 ℃; for 1.5h; Inert atmosphere;

(2-(1E,3Z)-4-iodo-3-methylbuta-1,3-dien-1-yl)-1,3,3-trimethylcyclohex-1-ene; Further stages;

DOI:10.1002/chem.201903080

upstream raw materials:

beta-carotene

7-cis-β-carotene

β-Carotin

hydrogenchloride

Downstream raw materials:

beta-carotene

9,13'-di-cis-β,β-Carotin

9,13-di-cis-β-carotene

9,15-di-cis-β-carotene

Refernces

• 1、 Schrenk,Silker,King. "-". . p. 328. Retrieved 1944.
• 2、 Yang, Cheng,Yan, Hongxiao,Jiang, Xin,Xu, Huaneng,Tsao, Rong,Zhang, Lianfu. "Preparation of 9 Z-β-Carotene and 9 Z-β-Carotene High-Loaded Nanostructured Lipid Carriers: Characterization and Storage Stability". . p. 13844 - 13853. Retrieved 2020.
• 3、 Achir, Nawel,Penicaud, Caroline,Avallone, Sylvie,Bohuon, Philippe. "Insight into β-carotene thermal degradation in oils with multiresponse modeling". . p. 2035 - 2045. Retrieved 2011.
• 4、 Rivas, Aurea,Pérez-Revenga, Víctor,Alvarez, Rosana,de Lera, Angel R.. "Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids". . p. 14399 - 14407. Retrieved 2019/11/03.