9-cis Retinoyl b-D-Glucuronide

Base Information

• Chemical Name: 9-cis Retinoyl b-D-Glucuronide
• CAS No.: 153321-67-6
• Molecular Formula: C₂₆H₃₆O₈
• Molecular Weight: 476.567
• Hs Code.: 29389090
• Mol file: 153321-67-6.mol

Synonyms:Retinoicacid, b-D-glucopyranuronic acid deriv.;9-cis-Retinoyl-b-D-glucuronide

Chemical Property of 9-cis Retinoyl b-D-Glucuronide

Chemical Property:

• Boiling Point: 670.4±55.0 °C(Predicted)
• PKA: 2.66±0.70(Predicted)
• PSA: 116.45000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 3.42680

Purity/Quality:

98% ^*data from raw suppliers

9-cis-Retinoyl b-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of 9-cis-Retinoic acid A metabolite of 9-cis-Retinoic acid.

Technology Process of 9-cis Retinoyl b-D-Glucuronide

There total 5 articles about 9-cis Retinoyl b-D-Glucuronide 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: 35.0%

D-glucuronic acid (489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + retinoyl fluoride (83802-77-1) → Retinoic Acid glucuronide (153321-67-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; for 42h;

Reference yield:

13-cis-retinoic acid (4759-48-2) → 13-cis-Retinoic acid glucuronide (153321-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylaminosulfur trifluoride / diethyl ether / -70 °C

2: NaHCO₃ / acetone; H₂O / Ambient temperature

With diethylamino-sulfur trifluoride; sodium hydrogencarbonate; In diethyl ether; water; acetone;

DOI:10.1080/00397919608003496

Reference yield:

9-cis-retinoic acid (302-79-4,3555-80-4,4759-48-2,5300-03-8,5352-74-9,68070-34-8,68070-35-9,97950-17-9,98462-64-7,124510-04-9) → (2S,3S,4S,5R,6S)-6-[(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid (153321-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylaminosulfur trifluoride / diethyl ether / -70 °C

2: NaHCO₃ / acetone; H₂O / Ambient temperature

With diethylamino-sulfur trifluoride; sodium hydrogencarbonate; In diethyl ether; water; acetone;

DOI:10.1080/00397919608003496

upstream raw materials:

D-glucuronic acid

retinoyl fluoride

β-D-glucuronic acid sodium salt

9-cis-retinoic acid

Refernces

• 1、 Biesalski, Hans-K.,Doepner, Gudrun,Kunz, Horst,Paust, Joachim,John, Michael. "Convenient Synthesis of Biologically Important Retinoids". . p. 717 - 720. Retrieved 2007/10/02.