Transcrocetin sodium

Base Information

• Chemical Name: Transcrocetin sodium
• CAS No.: 27876-94-4
• Molecular Formula: C20H24O4
• Molecular Weight: 328.408
• Hs Code.: 29171900
• NSC Number: 407300
• Wikidata: Q76390044
• ChEMBL ID: CHEMBL1993367
• Mol file: 27876-94-4.mol

Synonyms:HSDB 1949;8022-19-3;.alpha.-Crocetin;NSC407300;(2Z,4E,6Z,8E,10Z,12E,14Z)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid;Transcrocetin sodium;8,.psi.-carotenedioic acid;CHEMBL1993367;2,6,8,10,12,14-Hexadecaheptaenedioic acid, 2,6,11,15-tetramethyl-;2,6,8,10,12,14-Hexadecaheptaenedioic acid, 2,6,11,15-tetramethyl-, (all-E)-

Chemical Property of Transcrocetin sodium

Chemical Property:

• Appearance/Colour: Red solid
• Vapor Pressure: 3.32E-15mmHg at 25°C
• Melting Point: 285 ºC
• Refractive Index: 1.558
• Boiling Point: 585.1°C at 760 mmHg
• PKA: 4.39±0.19(Predicted)
• Flash Point: 321.7 °C
• PSA: 74.60000
• Density: 1.085 g/cm³
• LogP: 4.60940
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 328.16745924
• Heavy Atom Count: 24
• Complexity: 608

Purity/Quality:

95%-98% ^*data from raw suppliers

Crocetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: CC(=CC=CC=C(C)C=CC=C(C)C(=O)O)C=CC=C(C)C(=O)O
• Isomeric SMILES: C/C(=C/C=C/C=C(\C=C\C=C(/C(=O)O)\C)/C)/C=C/C=C(\C(=O)O)/C
• Uses: Experimental treatment of arteriosclerosis by increasing oxygen diffusion through arterial walls, thus decreasing buildup of cholesterol. Crocetin is a carotenoid derived from saffron, and is shown to have anticancer effects in both human adenocarcinoma gastric cancer cells and rat model of gastric cancer.

Technology Process of Transcrocetin sodium

There total 15 articles about Transcrocetin sodium 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:

crocin (42553-65-1,91740-80-6) → crocetin (27876-94-4)

Guidance literature:

crocin; With sodium hydroxide; water; at 50 ℃; for 3.5h;

With phosphoric acid; In water; at 20 ℃; for 3h;

Reference yield:

crocin-4 (55750-86-2) → crocetin (27876-94-4)

Guidance literature:

With water; sodium hydroxide; at 60 ℃; for 4h;

DOI:10.1016/j.fitote.2018.06.012

Reference yield:

(2E,4E,6E,10E,12E,14E)-2,6,11,15-Tetramethyl-hexadeca-2,4,6,10,12,14-hexaen-8-ynedioic acid ethyl ester 2-formyl-2-hydroxy-1,3,3-trimethyl-cyclohexyl ester (35482-80-5) → crocetin (27876-94-4)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst;

DOI:10.1002/hlca.19710540808

upstream raw materials:

(2E,4E,6E,10E,12E,14E)-2,6,11,15-Tetramethyl-hexadeca-2,4,6,10,12,14-hexaen-8-ynedioic acid ethyl ester 2-formyl-2-hydroxy-1,3,3-trimethyl-cyclohexyl ester

crocin

<3-(Methoxycarbonyl)-2-butenyl>triphenylphosphoniumbromid

2-methyl-4-(triphenyl-λ⁵-phosphoranylidene)but-2-enoic acid methyl ester

Downstream raw materials:

Crocetindimethylester

Refernces

• 1、 Shakya, Rajina,Nepal, Mahesh R.,Kang, Mi Jeong,Jeong, Tae Cheon. "Effects of intestinal microbiota on pharmacokinetics of crocin and crocetin in male sprague-dawley rats". . p. 1 - 10. Retrieved 2020.
• 2、 Chen, Guihua,Deng, Zhaoyang,Li, Ling,Liu, Yuxiu,Wang, Qingmin,Xu, Changjiang,You, Shengyong,Zou, Jiyong. "Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters". . p. 13637 - 13643. Retrieved 2021/11/18.