15-cis-Phytoene

Base Information

• Chemical Name: 15-cis-Phytoene
• CAS No.: 13920-14-4
• Molecular Formula: C40H64
• Molecular Weight: 544.948
• UNII: 876K2ZK1OF
• DSSTox Substance ID: DTXSID10433340
• Nikkaji Number: J39.585D
• Wikipedia: Phytoene
• Wikidata: Q302247
• NCI Thesaurus Code: C126901
• Metabolomics Workbench ID: 28980
• Mol file: 13920-14-4.mol

Synonyms:(all-E) phytoene;15-cis-phytoene;7,7',8,8',11,11',12,12'-octahydro-psi,psi-carotene;all-trans-phytoene;phytoene;phytoene, (15-cis)-isomer;phytoene, (all-E)-;phytoene, (cis)-isomer;trans-phytoene

Chemical Property of 15-cis-Phytoene

Chemical Property:

• Boiling Point: 620.3°Cat760mmHg
• Flash Point: 333°C
• PSA: 0.00000
• Density: 0.865g/cm³
• LogP: 13.83400
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 15.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 20
• Exact Mass: 544.500802041
• Heavy Atom Count: 40
• Complexity: 887

Purity/Quality:

99% ^*data from raw suppliers

15-cis-Phytoene(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/C=C\C=C(\CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)/C)/C)C
• Uses: 15-cis-Phytoene is an intermediate in the biosynthesis of carotenoids. Intermediate in the biosynthesis of carotenoids

Technology Process of 15-cis-Phytoene

There total 11 articles about 15-cis-Phytoene 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: 80.0%

((6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,10,14,16,18,22,26,30-nonaene-16-sulfonyl)-benzene (116059-44-0,116127-26-5) → phytoene (540-04-5,7699-28-7,13832-76-3,13920-14-4,42482-95-1,115648-62-9)

Guidance literature:

With bis(acetylacetonate)nickel(II); butyl magnesium bromide; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(01)91350-4

Reference yield: 74.0%

(((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)sulfonyl)benzene (38818-91-6) → phytoene (540-04-5,7699-28-7,13832-76-3,13920-14-4,42482-95-1,115648-62-9)

Guidance literature:

With bis(acetylacetonate)nickel(II); isopropylmagnesium bromide; In tetrahydrofuran; for 6h; Heating;

Reference yield: 70.7%

all-E 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentanenal (93040-98-3) + triphenyl-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-phosphonium; bromide (57784-37-9) → phytoene (540-04-5,7699-28-7,13832-76-3,13920-14-4,42482-95-1,115648-62-9)

Guidance literature:

triphenyl-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-phosphonium; bromide; With n-butyllithium; In diethyl ether; hexane; at 0 - 5 ℃; for 0.5h;

all-E 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentanenal; In diethyl ether; hexane; at 0 - 5 ℃; for 1.5h;

upstream raw materials:

2E,6E,10E-geranylgeranyl aldehyde

triphenyl-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-phosphonium; bromide

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

Geranylgeraniol

Downstream raw materials:

15-cis-phytofluene

all-(E)-phytofluene

Refernces

• 1、 -. "METHOD FOR THE PRODUCTION OF PHYTOFLUENE". Page/Page column 11. . Retrieved 2010/02/11.
• 2、 Capet, M.,Cuvigny, T.,Penhoat, C. Herve du,Julia, M.,Loomis, G.. "Syntheses with Sulfones L : Preparation of β-Hydroxysulfones through the Combined Oxidative Desulfonylation/Condensation Reaction of Sulfonyl Anions. Application to Terpene Synthesis.". . p. 6273 - 6276. Retrieved 2007/10/02.