Cryptoxanthin

Base Information

• Chemical Name: Cryptoxanthin
• CAS No.: 472-70-8
• Molecular Formula: C40H56 O
• Molecular Weight: 552.884
• Hs Code.: 29062990
• UNII: 6ZIB13GI33
• DSSTox Substance ID: DTXSID30912309
• Metabolomics Workbench ID: 28994
• Nikkaji Number: J5.952H
• Wikidata: Q392062
• Mol file: 472-70-8.mol

Synonyms:Beta Cryptoxanthin;Beta-Cryptoxanthin

Chemical Property of Cryptoxanthin

Chemical Property:

• Vapor Pressure: 1.35E-21mmHg at 25°C
• Melting Point: 167℃
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 682.9°Cat760mmHg
• PKA: 14.90±0.70(Predicted)
• Flash Point: 293.8°C
• PSA: 20.23000
• Density: 0.974g/cm³
• LogP: 11.57660
• Storage Temp.: −20°C
• Solubility.: chloroform: soluble1mg/mL
• XLogP3: 12.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 552.433116406
• Heavy Atom Count: 41
• Complexity: 1250

Purity/Quality:

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

(3R)-β-Cryptoxanthin ^*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=CC2=C(CC(CC2(C)C)O)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(C[C@H](CC2(C)C)O)C)/C)/C
• Recent ClinicalTrials: Beta-cryptoxanthin Supplement: Absorption and Function
• Uses: A natural caratenoid pigment that is converted to Vitamin A in the human body. It is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA. A potential chemopreventative agent against lung cancer as well as other types of cancer. β-Cryptoxanthin has also been used to study its effect on the production of immunoglobulins in Peyer′s patch cells ex- vivo. It has also been used as a standard in high-performance liquid chromatography (HPLC analysis).(5)

Technology Process of Cryptoxanthin

There total 50 articles about Cryptoxanthin 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: 70.0%

12'-apo-β-caroten-12'-al (1638-05-7) + <(2Z,4E)-5-<(R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methylpenta-2,4-dienyl>triphenylphosphonium chloride (130696-70-7) → (3R)-cryptoxanthin (472-70-8)

Guidance literature:

With ethyloxirane; In ethanol; Reflux; Inert atmosphere;

Reference yield: 70.0%

12'-apo-β-caroten-12'-al (1638-05-7) + [(2E,4E)-(R)-5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium chloride (76686-31-2) → (3R)-cryptoxanthin (472-70-8)

Guidance literature:

With ethyloxirane; In ethanol; for 6h; optical yield given as %ee; Inert atmosphere; Reflux;

DOI:10.1055/s-0030-1258382

Reference yield: 57.0%

C23H34OSi2 + 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene (138846-06-7) + (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol (444122-16-1) → (3R)-cryptoxanthin (472-70-8)

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;

(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol; Further stages;

DOI:10.1002/chem.201903080

upstream raw materials:

(3R)-β-cryptoxanthin palmitate

(3R,6'R)-3-hydroxy-3',4'-didehydro-β,γ-carotene

(3R)-3-hydroxy-3',4'-didehydro-β,β-carotene

(3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene

Downstream raw materials:

β-cryptoxanthin monosuccinate

C₈₄H₁₁₄O₄

C₆₄H₈₈O₄

β-cryptoxanthin pentynoate

Refernces

• 1、 -. "Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin". . . Retrieved 2012/07/27.
• 2、 -. "Process For The Preparation of Beta and Alpha Cryptoxanthin". Page/Page column title page; 3; 7; 11-12. . Retrieved 2010/12/29.