Dimethyl Sulfoxide → HCID 6510267, compound

HRID 1415703Notes

Reaction equation

HRID 1415703 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18][OH:19].CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=[O:40].CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C(O)=O.CS(C)=O>CO>[CH3:1][C:2]1=[CH:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])/[C:3]/1=[CH:10]/[CH:11]=[C:12](/[CH:13]=[CH:14]/[CH:15]=[C:16](/[CH:17]([OH:40])[CH2:18][OH:19])\[CH3:20])\[CH3:21]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 444795Retinoic AcidHCID 445354RetinolHCID 638015Retinal

Product 1

HCID 6510267HCID 6510267, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

All-trans retinol, all-trans retinal and all-trans retinoic acid were purchased from Sigma Chemical Co. (St. Louis, Mo.). The retinoids were dissolved at a concentration of 3×10-2M in methanol or DMSO with 10-4M butylated hydroxytoluene (Sigma Chemical Co.) added and stored in the dark at -20° C. in a nitrogen atmosphere. Immediately before use, the stock solutions were diluted in serum-free medium. 14-Hydroxy-retro-retinol (14HRR) was isolated from the pellets of HeLa cells fed with retinol by using a series of reversed-phase HPLC columns as described (33). 14HRR was pure according to the retention time on an analytical C18 reversed-phase column and the typical UV absorption spectrum.

Workup

  1. customdark at -20° C.
  2. additionImmediately before use, the stock solutions were diluted in serum-free medium

Sources & evidence

ORD record
ord-6c38ccb748b04820a03706ae8153a986
Source dataset
uspto-grants-1999_06
Patent number
US05908868

Reaction notes

Loading…