Bimatoprost isopropyl ester CAS#: 130209-76-6 • ChemWhat中文网

Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

英文名	Bimatoprost isopropyl ester
IUPAC Name	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
分子结构
CAS编号	130209-76-6
MDL Number	MFCD00902150
别名	130209-76-6 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
分子式	C₂₆H₃₈O₅
分子量	430.6
InChI	InChI=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 Key	JGZRPRSJSQLFBO-FWPUOYPASA-N
Isomeric SMILES	CC(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 ID	Title	Publication Date
US2016/106651	COMPOSITIONS AND METHODS FOR TREATING HAIR LOSS USING NON-NATURALLY OCCURRING PROSTAGLANDINS	2016
WO2009/35565	PROSTAGLANDIN ANALOGUES FOR IMPLANT DEVICES AND METHODS	2009
US2009/259058	Process for the Preparation of Prostaglandin Analogues and Intermediates Thereof	2009

Appearance

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

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)
Chemical shifts	1H	CDCl3
Chemical shifts	13C	CDCl3

Conditions

Yield

In methanol at 80℃; for 24 – 48h;

Experimental Procedure
Example 4. Preparation of 17-phenyl trinor PGF_2α isobutyl amide from ester A solution of 17-phenyl- 13,14-dihydro trinor PGF_2α 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 PGF_2α isobutyl amide (> 80% yield).

80%

Pictogram(s)
Signal	Danger
GHS Hazard Statements	H302+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 Codes	P203, 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.)

HS Code
Storage	Store -10°C for long time, in container tightly sealed; Protect from light and moisture.
Shelf Life	2 year
Market Price

Druglikeness
Lipinski rules component
分子量	430.585
logP	4.145
HBA	5
HBD	3
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	86.99
Rotatable Bond (RotB)	13
Matching Veber Rules	1

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.