trans-Latanoprost Acid

Base Information

• Chemical Name: trans-Latanoprost Acid
• CAS No.: 41639-83-2
• Molecular Formula: C23H34O5
• Molecular Weight: 390.52
• Hs Code.: 2937500000
• European Community (EC) Number: 682-021-0
• Nikkaji Number: J808.609E
• Mol file: 41639-83-2.mol

Synonyms:trans-Latanoprost Acid;903549-49-5;(E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid;41639-83-2;trans-atanoprost Acid;SCHEMBL1313164;SCHEMBL1514743;HMS3648E09;PDSP2_001705;AKOS015895165;PD021417;SR-01000946203;SR-01000946203-1

Chemical Property of trans-Latanoprost Acid

Chemical Property:

• Appearance/Colour: Pale yellow oil
• Vapor Pressure: 1.09E-15mmHg at 25°C
• Refractive Index: 1.564
• Boiling Point: 609.1 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 336.2 °C
• PSA: 97.99000
• Density: 1.16 g/cm³
• LogP: 3.31940
• Storage Temp.: −20°C
• Solubility.: DMSO: freely soluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 472

Purity/Quality:

98% ^*data from raw suppliers

Latanoprost acid ^*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: C1C(C(C(C1O)CC=CCCCC(=O)O)CCC(CCC2=CC=CC=C2)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@H]1O)C/C=C/CCCC(=O)O)CC[C@H](CCC2=CC=CC=C2)O)O
• Description: Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (free acid) by endogenous esterase enzymes. The free acid form is 200 times more potent than latanoprost as an FP receptor ligand for the human recombinant FP receptor. Latanoprost is the isopropyl ester of a PGF2α analog containing an aromatic group (17-phenyl) in the ω-chain. Lat-FA is the corresponding carboxylic acid of this analog. Lat-FA is a potent FP receptor agonist with an EC50 of 3.6 nM for human FP receptors, which is twice the potency of PGF2α. The efficacy of PG analog esters for the treatment of glaucoma correlates closely with the FP receptor binding affinity of the free acid. However, Lat-FA is more irritating and less effective than the prodrug latanoprost when applied directly to the eyes of human glaucoma patients.
• Uses: A metabolite of Latanoprost A metabolite of Latanoprost. Potent, selective FP prostanoid receptor agonist. F-series Prostaglandin analog. 200 times as potent as isopropyl ester form. Latanoprost USP Related Compound E.

Technology Process of trans-Latanoprost Acid

There total 89 articles about trans-Latanoprost Acid 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: 100.0%

latanoprost (130209-82-4,145773-22-4,913258-34-1) → latanoprost acid (41639-83-2)

Guidance literature:

With sodium hydroxide; In methanol; for 16h;

Reference yield: 99.0%

(Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate (913258-32-9) → latanoprost acid (41639-83-2)

Guidance literature:

With lithium hydroxide; In methanol; water; for 8h;

DOI:10.1002/ejoc.200600749

Reference yield: 96.0%

methyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate (913258-31-8) → latanoprost acid (41639-83-2)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃; for 20h;

DOI:10.1002/ejoc.200600749

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

methyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate

(Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

(S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane

Downstream raw materials:

17-phenyl-13,14-dihydro-trinor-prostaglandin F2α isobutylamide

17-phenyl-13,14-dihydro-trinor-prostaglandin F2α isobutyl ester

latanoprost

4-(nitrooxy)butyl [1α(Z),2β(R),3α,5α]-7-[3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl]-5-heptenoate

Refernces

• 1、 Hayashi, Yujiro,Umekubo, Nariyoshi. "Asymmetric Synthesis of Corey Lactone and Latanoprost". supporting information. p. 6221 - 6227. Retrieved 2020/09/21.
• 2、 -. "High-purity Latanoprost, preparation method therefor and use of Latanoprost". Paragraph 0092; 0093. . Retrieved 2017/12/01.