ABC00809SL

5-trans-LATANOPROST (Crude)

5-trans-LATANOPROST (Crude) is a stereoisomeric impurity of latanoprost, featuring a trans-configuration at the 5(6)-ring junction compared to the parent drug's cis-geometry. It retains the key structural elements of latanoprost, including a 1,3-dioxane core, a cyclopropane ring, and a carboxylic ester moiety. The trans-geometry alters its conformational flexibility and pharmacophoric alignment, rendering it inactive as a prostaglandin F2ฮฑ analog. This compound arises during synthetic processes involving asymmetric hydrogenation steps. It serves as a critical HPLC reference standard for quantifying stereoisomeric impurities in latanoprost active pharmaceutical ingredient batches.

On Request
Molecular Formula C26H40O5
Molecular Weight 432.6000
CAS Number 913258-34-1 โœ“ Verified
PubChem CID 5282380 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Latanoprost
Lead Time On Request
IUPAC Name propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
Official Reference Standards
Std Catalog # Quantity Price
USP 1357486 โ†— 50 mg USD 1261.00

๐Ÿ“ Synonyms

913258-34-1 trans-Latanoprost 5,6-trans-Latanoprost Latanoprost, (5E)- ZC39I2T1VW LATANOPROST IMPURITY F [EP IMPURITY] 5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester, (5E)- Isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate LATANOPROST IMPURITY F (EP IMPURITY) RefChem:798533

๐Ÿ”ฌ Chemical Identifiers

CC(C)OC(=O)CCC/C=C/C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3+/t21-,22+,23+,24-,25+/m0/s1
GGXICVAJURFBLW-RDSJPUOVSA-N

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