Product Name

  • Name

    Carboprost

  • EINECS
  • CAS No. 35700-23-3
  • Article Data8
  • CAS DataBase
  • Density 1.139 g/cm3
  • Solubility soluble in water
  • Melting Point 79-82 °C
  • Formula C21H36O5
  • Boiling Point 536.562 °C at 760 mmHg
  • Molecular Weight 368.514
  • Flash Point 292.373 °C
  • Transport Information
  • Appearance Off-white solid
  • Safety
  • Risk Codes R36
  • Molecular Structure Molecular Structure of 35700-23-3 (Carboprost)
  • Hazard Symbols Xi
  • Synonyms (15S)-15-Methyl-PGF2α;(15S)-15-Methylprostaglandin F2α;15-Methyl-PGF2α;15-Methylprostaglandin F2α;U 32921;
  • PSA 97.99000
  • LogP 3.43300

Synthetic route

U 36384
35700-21-1

U 36384

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With water; sodium hydroxide In methanol98%
C27H50O5Si

C27H50O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;85%
C30H56O5Si

C30H56O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;85%
C24H44O5Si

C24H44O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;85%
C27H50O5Si

C27H50O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;85%
C23H40O6

C23H40O6

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 55℃; for 10h;85%
C25H44O6

C25H44O6

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 55℃; for 10h;85%
C37H54O5Si

C37H54O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h;84%
(4-carboxybutyl)triphenylphosphonium bromide
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

C16H28O4

C16H28O4

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -10 - -5℃; for 12.1667h; Inert atmosphere;77%
(15S)-15-methyl-PGF2α 1,11-lactone 9,15-bis(tert-butyldimethylsilyl ether)
85720-21-4

(15S)-15-methyl-PGF2α 1,11-lactone 9,15-bis(tert-butyldimethylsilyl ether)

A

Carboprost
35700-23-3

Carboprost

B

(15S)-15-methyl-PGF2α 1,11-lactone
80029-28-3

(15S)-15-methyl-PGF2α 1,11-lactone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In 1,2-dimethoxyethane for 16h; Heating;A 42%
B 46%
(15S)-15-methyl prostaglandin F2α methyl ester
96744-82-0

(15S)-15-methyl prostaglandin F2α methyl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 81 percent / pyridine / 1.) 0 deg C, 5 h, 2.) 25 deg C, 18 h
2: 60 percent / imidazole / dimethylformamide / 16 h / 80 °C
3: 89 percent / Zn, CH3OH / 1.25 h / Heating
4: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
5: xylene / 36 h / Heating
6: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(15S)-15-methyl-PGF2α methyl ester 11-(trichloroethylcarbonate)
85720-17-8

(15S)-15-methyl-PGF2α methyl ester 11-(trichloroethylcarbonate)

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 60 percent / imidazole / dimethylformamide / 16 h / 80 °C
2: 89 percent / Zn, CH3OH / 1.25 h / Heating
3: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
4: xylene / 36 h / Heating
5: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether)
85720-19-0

(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether)

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
2: xylene / 36 h / Heating
3: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(Z)-7-{(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enethioic acid S-pyridin-2-yl ester

(Z)-7-{(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enethioic acid S-pyridin-2-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: xylene / 36 h / Heating
2: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether) 11-(trichloroethyl carbonate)
85720-18-9

(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether) 11-(trichloroethyl carbonate)

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / Zn, CH3OH / 1.25 h / Heating
2: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
3: xylene / 36 h / Heating
4: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(3aR,4R,5R,6aS)-5-triethylsilyloxy-4-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]hexahydro-2H-cyclopenta[b]furan-2-ol
1036855-83-0

(3aR,4R,5R,6aS)-5-triethylsilyloxy-4-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]hexahydro-2H-cyclopenta[b]furan-2-ol

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Wittig Reaction;
Multi-step reaction with 3 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
1.2: 4 h / 20 °C
2.1: sodium carbonate / acetonitrile; water / 4 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-hydroxy-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-hydroxy-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / methanol / 40 °C / Large scale
2: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
3: potassium carbonate / acetone / 50 °C / Large scale
4: sodium hydroxide; water / methanol
View Scheme
(3aR,4R,5R,6aS)-hexahydro-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-2,5-diol

(3aR,4R,5R,6aS)-hexahydro-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-2,5-diol

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
2: potassium carbonate / acetone / 50 °C / Large scale
3: sodium hydroxide; water / methanol
View Scheme
(5Z,9α,11α,13E)-15-methyl-9,11,15-trihydroxy-prosta-5,13-diene-1-carboxylic acid
41691-84-3

(5Z,9α,11α,13E)-15-methyl-9,11,15-trihydroxy-prosta-5,13-diene-1-carboxylic acid

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 50 °C / Large scale
2: sodium hydroxide; water / methanol
View Scheme
[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester
31753-00-1

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: (S,S)-taddol / toluene / -50 °C / Inert atmosphere; Large scale
2: diisobutylaluminium hydride / toluene; tetrahydrofuran / -75 °C / Inert atmosphere; Large scale
3: potassium carbonate / methanol / 40 °C / Large scale
4: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
5: potassium carbonate / acetone / 50 °C / Large scale
6: sodium hydroxide; water / methanol
View Scheme
[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -75 °C / Inert atmosphere; Large scale
2: potassium carbonate / methanol / 40 °C / Large scale
3: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
4: potassium carbonate / acetone / 50 °C / Large scale
5: sodium hydroxide; water / methanol
View Scheme
(4-carboxybutyl)triphenylphosphonium bromide

(4-carboxybutyl)triphenylphosphonium bromide

C16H28O4

C16H28O4

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at -10 - -5℃; for 0.166667h; Wittig Olefination; Inert atmosphere;
Stage #2: C16H28O4 In tetrahydrofuran at -5℃; for 12h;		10.8 g
3α,5α-Dihydroxy-2β-(3'-oxo-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether
64072-25-9

3α,5α-Dihydroxy-2β-(3'-oxo-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 6 h / -50 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
3.2: 4 h / 20 °C
4.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
C22H40O4Si

C22H40O4Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
2.2: 4 h / 20 °C
3.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
C22H42O4Si

C22H42O4Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
1.2: 4 h / 20 °C
2.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
C28H52O5Si

C28H52O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
Carboprost
35700-23-3

Carboprost

2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

carboprost tromethamine

carboprost tromethamine

Conditions
ConditionsYield
In methanol at 20℃; for 2h;100%
In isopropyl alcohol at 20℃; for 1h;
Carboprost
35700-23-3

Carboprost

(Z)-(1R,3aS,11aR)-1-((E)-(S)-3-Hydroxy-3-methyl-oct-1-enyl)-1,3,3a,6,7,8,11,11a-octahydro-4-oxa-cyclopentacyclodecene-2,5-dione
85235-19-4

(Z)-(1R,3aS,11aR)-1-((E)-(S)-3-Hydroxy-3-methyl-oct-1-enyl)-1,3,3a,6,7,8,11,11a-octahydro-4-oxa-cyclopentacyclodecene-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / 2,2'-dipyridyl disulfide, PPh3 / xylene / a) 25 deg C, 18 h, b) reflux, 4 h
2: 440 mg / H2CrO4, H2SO4 / acetone / a) -40 deg C, 2 h, b) -30 deg C, 1.5 h
View Scheme
Carboprost
35700-23-3

Carboprost

(15S)-15-methyl-9-deoxy-Δ9-PGD2
85235-20-7

(15S)-15-methyl-9-deoxy-Δ9-PGD2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / 2,2'-dipyridyl disulfide, PPh3 / xylene / a) 25 deg C, 18 h, b) reflux, 4 h
2: 440 mg / H2CrO4, H2SO4 / acetone / a) -40 deg C, 2 h, b) -30 deg C, 1.5 h
3: 190 mg / silica gel / ethyl acetate; methanol
View Scheme
Carboprost
35700-23-3

Carboprost

U 36384
35700-21-1

U 36384

Carboprost Specification

The Carboprost, with the CAS registry number 35700-23-3, is also known as (15S)-15-Methylprostaglandin F2α. It belongs to the product categories of Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C21H36O5 and molecular weight is 368.51. What's more, its systematic name is (5E,9α,11α,13E,15S)-9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic acid. Its classification codes are: (1)Abortifacient Agents; (2)Abortifacient agents, nonsteroidal; (3)Hormone; (4)Human Data; (5)Oxytocic; (6)Oxytocics; (7)Reproductive Control Agents; (8)Reproductive Effect. This chemical is a nonsteroidal abortifacient agent that is effective in both the first and second trimesters of pregnancy. It is a synthetic prostaglandin analogue of PGF2α (specifically, it is 15-methyl-PGF2α) with oxytocic properties. Carboprost induces contractions and can trigger abortion in early pregnancy. It also reduces postpartum bleeding.

Physical properties of Carboprost are: (1)ACD/LogP: 2.493; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.68; (4)ACD/LogD (pH 7.4): -0.12; (5)ACD/BCF (pH 5.5): 7.12; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 83.29; (8)ACD/KOC (pH 7.4): 1.33; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 15; (12)Polar Surface Area: 97.99 Å2; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 105.396 cm3; (15)Molar Volume: 323.516 cm3; (16)Polarizability: 41.782×10-24cm3; (17)Surface Tension: 47.4 dyne/cm; (18)Density: 1.139 g/cm3; (19)Flash Point: 292.373 °C; (20)Enthalpy of Vaporization: 93.532 kJ/mol; (21)Boiling Point: 536.562 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCC/C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@](O)(C)CCCCC
(2)Std. InChI: InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5+,14-12+/t16-,17-,18+,19-,21+/m1/s1
(3)Std. InChIKey: DLJKPYFALUEJCK-MRVZPHNRSA-N 

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