66592-72-1

Basic information

• Product Name: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid
• Synonyms: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid;4-Hydroxyretinoic acid;all-trans 4-Hydroxy Retinoic Acid;rac all-trans;rac all-trans 4-Hydroxy Retinoic Acid;4-Hydroxy-all-trans-Retinoic Acid
• CAS NO: 66592-72-1
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.43
• Product Categories: Intermediates & Fine Chemicals;Isotope Labelled Compounds;Metabolites & Impurities;Pharmaceuticals;Retinoids
• Mol File: 66592-72-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 506.5°C at 760 mmHg
• Flash Point: 274.2°C
• Appearance: /
• Density: 1.075g/cm³
• Vapor Pressure: 2.22E-12mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.73±0.33(Predicted)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid(66592-72-1)
• EPA Substance Registry System: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid(66592-72-1)

Safety Data

• Hazardous Substances Data: 66592-72-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

A labelled metabolite of all-trans Retinoic acid (R250200).

Definition

ChEBI: A retinoid that consists of all-trans-retinoic acid bearing a hydroxy substituent at position 4 on the cyclohexenyl ring.

InChI:InChI=1/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

Upstream product

• 68-26-8 RETINOL 
• 116-31-4 all-trans-Retinal 
• 302-79-4 all-trans-retinoic-acid 
• 38030-57-8 4-ketoretinoic acid 
• 72526-76-2 ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 63184-93-0 (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide 
• 81121-19-9 (2E,4E,6E,8E)-9-(3-Acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 81121-21-3 rac-(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid ethyl ester 

Downstream Products

• 1425830-36-9 C₂₀H₂₈O₃ 
• 1425830-47-2 C₂₀H₂₈O₃ 
• 81121-27-9 rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid 
• 38030-57-8 4-ketoretinoic acid 
• 38030-59-0 4-Hydroxyretinoic acid methyl ester 

Relevant articles and documents

CYP26C1 is a hydroxylase of multiple active retinoids and interacts with cellular retinoic acid binding proteins

The clearance of retinoic acid (RA) and its metabolites is believed to be regulated by the CYP26 enzymes, but the specific roles of CYP26A1, CYP26B1, and CYP26C1 in clearing active vitamin A metabolites have not been defined. The goal of this study was to

A sensitive and specific method for measurement of multiple retinoids in human serum with UHPLC-MS/MS

Retinol (vitamin A) circulates at 1-4 μM concentration and is easily measured in serum. However, retinol is biologically inactive. Its metabolite, retinoic acid (RA), is believed to be responsible for biological effects of vitamin A, and hence the measurement of retinol concentrations is of limited value. A UHPLC-MS/MS method using isotope-labeled internal standards was developed and validated for quantitative analysis of endogenous RA isomers and metabolites. The method was used to measure retinoids in serum samples from 20 healthy men. In the fed state, the measured concentrations were 3.1 ± 0.2 nM for at RA, 0.1 ± 0.02 nM for 9-cisRA, 5.3 ± 1.3 nM for 13-cisRA, 0.4 ± 0.4 nM for 9,13-dicisRA, and 17.2 ± 6.8 nM for 4oxo-13-cisRA. The concentrations of the retinoids were not significantly different when measured after an overnight fast (3.0 ± 0.1 nM for atRA, 0.09 ± 0.01nM for 9-cisRA, 3.9 ± 0.2 nM for 13-cisRA, 0.3 ± 0.1 nM for 9,13-dicisRA, and 11.9 ± 1.6 nM for 4oxo-13-cisRA). 11-cisRA and 4OH-RA were not detected in human serum. The high sensitivity of the MS/MS method combined with the UHPLC separation power allowed detection of endogenous 9-cis RA and 4oxo-atRA for the first time in human serum. Copyright

All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use

Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.