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Latanoprost acid
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Name

Latanoprost acid

 EINECS N/A
CAS No. 41639-83-2 Density 1.16 g/cm3
PSA 97.99000 LogP 3.31940
Solubility DMSO: freely soluble Melting Point N/A
Formula C23H34O5 Boiling Point 609.1 °C at 760 mmHg
Molecular Weight 390.52 Flash Point 336.2 °C
Transport Information N/A Appearance Pale yellow oil
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 41639-83-2 (Latanoprost acid) Hazard Symbols N/A
Synonyms

5-Heptenoicacid, 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl]-, [1R-[1a(Z),2b(R*),3a,5a]]-;13,14-Dihydro-17-phenyl-18,19,20-trinor-PGF2a;PhXA 85;

Article Data 22

Latanoprost acid Synthetic route

913258-32-9

(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

41639-83-2

latanoprost acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water for 8h;99%
Stage #1: (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 With lithium hydroxide In methanol; water at 20℃; for 5.5 - 8h;
Stage #2: With sodium hydrogen sulfate; ammonium chloride In methanol; water; ethyl acetate Product distribution / selectivity;		99%
913258-31-8

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

41639-83-2

latanoprost acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water at 20℃; for 20h;96%
Stage #1: methyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate With lithium hydroxide In methanol; water at 20℃; for 20h;
Stage #2: With sodium hydrogen sulfate; ammonium chloride In methanol; water; ethyl acetate		96%
1240483-23-1

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid

41639-83-2

latanoprost acid

Conditions
ConditionsYield
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid With hydrogenchloride; water In tetrahydrofuran at 20℃; for 18h;
Stage #2: In tetrahydrofuran pH=6.8; Aqueous phosphate buffer;		91%
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid With hydrogenchloride In tetrahydrofuran; water at 20℃; for 18h;
Stage #2: In tetrahydrofuran; water pH=6.8; Aqueous phosphate buffer;		91%
130209-82-4

latanoprost

41639-83-2

latanoprost acid

Conditions
ConditionsYield
Stage #1: latanoprost With lithium hydroxide; water In tetrahydrofuran for 16h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water		90%

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

41639-83-2

latanoprost acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 17h;87%
With hydrogenchloride In methanol; water for 3.33333h;

(8aR,9R,10R,14aS,Z)-10-hydroxy-9-((3R)-3-hydroxy-5-phenylpentyl)-4,5,8,8a,9,10,11,11a-octahydrocyclopenta[b]oxecin-2(3H)-one

41639-83-2

latanoprost acid

Conditions
ConditionsYield
With water; potassium hydroxide In water; isopropyl alcohol at 50℃; for 2h; Reagent/catalyst; Temperature;68%
With potassium hydroxide In water; isopropyl alcohol at 50℃; for 2h;
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol

41639-83-2

latanoprost acid

Conditions
ConditionsYield
With potassium tert-butylate 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h; Multistep reaction;
913258-20-5

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

41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
913258-19-2

(S)-4-phenyl-1-(p-tolylsulfonyloxy)-2-(triethylsiloxy)butane

41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
2: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
930118-48-2

methyl (Z)-7-[(1R,2R,3R,5S)-2-((3S)-3-triethylsilyloxy-5-phenyl-1-(phenylsulfonyl)pentyl)-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-enoate

41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45 mg / PPTS / acetone; H2O / 6 h / 20 °C
2: 96 percent / LiOH*H2O / methanol; H2O / 20 h / 20 °C
View Scheme

Latanoprost acid Specification

The Latanoprost acid, with CAS registry number 41639-83-2, has the systematic name of (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoic acid. Besides this, it is also called 5-heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, (5Z)-. This chemical should be stored at the temperature of −20°C.

Physical properties of Latanoprost acid: (1)ACD/LogP: 2.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.41; (4)ACD/LogD (pH 7.4): -0.39; (5)ACD/BCF (pH 5.5): 4.42; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 59.25; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 15; (12)Polar Surface Area: 53.99 Å2; (13)Index of Refraction: 1.564; (14)Molar Refractivity: 109.55 cm3; (15)Molar Volume: 336.7 cm3; (16)Polarizability: 43.43×10-24cm3; (17)Surface Tension: 50 dyne/cm; (18)Enthalpy of Vaporization: 95.14 kJ/mol; (19)Vapour Pressure: 1.09E-15 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]2[C@@H](O)C[C@@H](O)[C@@H]2CC[C@@H](O)CCc1ccccc1
(2)InChI: InChI=1/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
(3)InChIKey: HNPFPERDNWXAGS-NFVOFSAMBJ
(4)Std. InChI: InChI=1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
(5)Std. InChIKey: HNPFPERDNWXAGS-NFVOFSAMSA-N

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