Bimatoprost isopropyl ester CAS#: 130209-76-6; ChemWhat Code: 416872

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameBimatoprost isopropyl ester
IUPAC Namepropan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoate
Molecular Structure17-PHENYL-TRINOR-PGF2ALPHA-IPR-CAS-130209-76-6
CAS Registry Number 130209-76-6
MDL NumberMFCD00902150
Synonyms130209-76-6
17-phenyl-trinor-PGF2alpha isopropyl ester
dehydrolatanoprost
Bimatoprost isopropyl ester
17-Phenyl trinor Pgf2alpha-Ipr
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoate
PhDH 100A
1IFH52MD8T
17-Phenyl-18,19,20-trinor-pgf2alpha-1-isopropyl ester
17-Phenyl trinor PGF2|A isopropyl ester
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-, 1-methylethyl ester, (5Z)-
17-phenyl-trinor-Prostaglandin F2alpha isopropyl ester
Phdh100A
isopropyl 9S,11R,15S-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate
130273-87-9
UNII-1IFH52MD8T
5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3S)-3-HYDROXY-5-PHENYL-1-PENTEN-1-YL)CYCLOPENTYL)-, 1-METHYLETHYL ESTER, (5Z)-
PGF2Alpha,17-phenyl
SCHEMBL1954979
CHEMBL2111623
BDBM85339
CHEBI:137717
JGZRPRSJSQLFBO-FWPUOYPASA-N
HMS3648J18
BCP29022
17-Phenyl-18,19,20-trinor-prostaglandin F2alpha-1-isopropyl ester
17-PHENYLTRINORPGF2ALPHA-IPR
LMFA03010124
AKOS040756131
HY-116161A
(1R-(1alpha(Z),2beta(1E,3S),3alpha,5alpha))-1-Methylethyl 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-5-heptenoate CAS_130209-76-6 CS-0128707 SR-01000946519 17-phenyl trinor Prostaglandin F2?? isopropyl ester SR-01000946519-1 Q27252458 17-PHENYL-18,19,20-TRINOR-PGF2.ALPHA.-1-ISOPROPYL ESTER ISOPROPYL PHENYLHYDROXYPENTENE DIHYDROXYCYCLOPENTYLHEPTENATE 17-phenyl trinor PGF2(c) paragraph sign-iPr;17-phenyl trinor PGF2(c) paragraph sign isopropyl ester 5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3S)-3-HYDROXY-5-PHENYL-1-PENTENYL)CYCLOPENTYL)-, 1-METHYLETHYL ESTER, (5Z)- 5-HEPTENOIC ACID, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-5-PHENYL-1-PENTENYL)CYCLOPENTYL)-, 1-METHYLETHYL ESTER, (1R-(1.ALPHA.(Z),2.BETA.(1E,3S),3.ALPHA.,5.ALPHA.))-
5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-, 1-methylethyl ester, (1R-(1alpha(Z),2beta(1E,3S*),3alpha,5alpha))-
Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3S,E)-3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl)-hept-5-enoate
PhDH 100A; 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-, 1-methylethyl ester, (5Z)-; 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-, 1-methylethyl
Molecular FormulaC26H38O5
Molecular Weight430.6
InChIInChI=1S/C26H38O5/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/h3,5-8,10-11,16-17,19,21-25,27-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t21-,22+,23+,24-,25+/m0/s1
InChI KeyJGZRPRSJSQLFBO-FWPUOYPASA-N 
Isomeric SMILESCC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
Patent Information
Patent IDTitlePublication Date
US2016/106651COMPOSITIONS AND METHODS FOR TREATING HAIR LOSS USING NON-NATURALLY OCCURRING PROSTAGLANDINS2016
WO2009/35565PROSTAGLANDIN ANALOGUES FOR IMPLANT DEVICES AND METHODS2009
US2009/259058Process for the Preparation of Prostaglandin Analogues and Intermediates Thereof2009

Physical Data

AppearancePale yellow to colorless oily liquid or pale yellow to white waxy solid

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts1HCDCl3
Chemical shifts13CCDCl3

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Bimatoprost isopropyl ester CAS 130209-76-6
Route of Synthesis (ROS) of Bimatoprost isopropyl ester CAS 130209-76-6
ConditionsYield
In methanol at 80℃; for 24 – 48h;

Experimental Procedure
Example 4. Preparation of 17-phenyl trinor PGF2α isobutyl amide from ester A solution of 17-phenyl- 13,14-dihydro trinor PGF2α isopropyl ester (43.3 mg, 0.1 mmol.) and isobutylamine (1.0 mL, 10.1 mmol.) in MeOH (4.0 mL) is heated to 80 0C for 24-48 hours. The reaction is cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, using CH2Cl2ZMeOH as eluent to afford 17-phenyl trinor PGF2α isobutyl amide (> 80% yield).		80%

Safety and Hazards

Pictogram(s)exclamation-markhealth-hazard
SignalDanger
GHS Hazard StatementsH302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]
Precautionary Statement CodesP203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

HS Code
StorageStore -10°C for long time, in container tightly sealed; Protect from light and moisture.
Shelf Life2 year
Market Price
Druglikeness
Lipinski rules component
Molecular Weight430.585
logP4.145
HBA5
HBD3
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)86.99
Rotatable Bond (RotB)13
Matching Veber Rules1
Use Pattern
Bimatoprost is widely used in the cosmetic field to promote eyelash growth. Its mechanism of action and effects are as follows:
Mechanism of Action
Bimatoprost prolongs the growth phase of eyelashes (the active phase in the eyelash growth cycle) and increases the number of hair follicles, stimulating natural eyelash growth. This mechanism significantly enhances eyelash density, length, and pigmentation.
Application Method
It is typically applied topically using a special applicator to place the solution at the base of the upper eyelashes (avoiding contact with the eyes and lower lashes). A common recommendation is to apply it once daily.
Effectiveness
Bimatoprost use generally starts to show results after 4–8 weeks, with optimal effects observed at 12–16 weeks. Eyelashes become noticeably longer, denser, and darker due to increased pigmentation, giving them a more prominent and defined appearance.

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