Product Name

  • Name

    cis-4-Hydroxy-L-proline

  • EINECS 210-542-1
  • CAS No. 618-27-9
  • Article Data25
  • CAS DataBase
  • Density 1.395 g/cm3
  • Solubility soluble in water
  • Melting Point 257 ºC (dec.)(lit.)
  • Formula C5H9NO3
  • Boiling Point 355.2 ºC at 760 mmHg
  • Molecular Weight 131.131
  • Flash Point 168.6 ºC
  • Transport Information
  • Appearance White to beige powder
  • Safety 24/25-36/37/39-27-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 618-27-9 (cis-4-Hydroxy-L-proline)
  • Hazard Symbols IrritantXi
  • Synonyms L-Proline,4-hydroxy-, cis-;Proline, 4-allo-hydroxy- (7CI);Proline, 4-allo-hydroxy-, L-(8CI);(2S,4S)-4-Hydroxyproline;(2S,4S)-4-Hydroxypyrrolidine-2-carboxylicacid;(S)-allo-Hydroxyproline;4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acid;4-cis-Hydroxy-L-proline;L-Allohydroxyproline;L-Proline, allo-hydroxy-;L-allo-4-Hydroxyproline;L-allo-Hydroxyproline;L-cis-4-Hydroxyproline;NSC206274;allo-4-Hydroxyproline;allo-Hydroxy-L-proline;allo-L-Hydroxyproline;cis-4-Hydroxyproline;cis-Hydroxyproline;Cis-L-4-Hydroxyproline;(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid;
  • PSA 69.56000
  • LogP -0.87740

Synthetic route

(2S,4S)-4-Benzoyloxy-pyrrolidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
157401-62-2

(2S,4S)-4-Benzoyloxy-pyrrolidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogenchloride at 140℃; for 3h;100%
L-proline
147-85-3

L-proline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; cis-4-proline hydroxylase; sodium L-ascorbate at 25℃; for 16h; stereospecific reaction;100%
With iron(II) sulfate; α-ketoglutaric acid disodium salt In culture medium at 28℃; for 72h; Enzymatic reaction; regioselective reaction;35%
With Mesorhizobium loti L-proline cis-4-hydroxylase; iron(II) sulfate at 25℃; for 20h; Reagent/catalyst; Enzymatic reaction; stereoselective reaction;
With hydrogenchloride; α-ketoglutaric acid; ammonium iron (II) sulfate; l-proline cis-4-hydroxylase; sodium L-ascorbate In aq. buffer at 21℃; for 14h; pH=6.5; Enzymatic reaction;> 95 %Chromat.
With ferrous(II) sulfate heptahydrate; α-ketoglutaric acid disodium salt; ascorbic acid In aq. phosphate buffer at 37℃; for 16h; pH=8; Enzymatic reaction;201 mg
(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline
13504-86-4

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 1h;87%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 4h;64%
With hydrogen bromide; acetic acid
With hydrogen; palladium on activated charcoal In water at 25℃; under 2660 Torr; for 3h;496 mg
(2S,4S)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)
132592-07-5

(2S,4S)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 2h; Ambient temperature;68%
(6S,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one
148429-59-8

(6S,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With water In isopropyl alcohol Ambient temperature;41%
N-acetyl-cis-4-hydroxy-L-proline
66267-44-5

N-acetyl-cis-4-hydroxy-L-proline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogenchloride
cis-1-ethoxycarbonyl-4-hydroxy-L-proline
19887-35-5, 118712-71-3

cis-1-ethoxycarbonyl-4-hydroxy-L-proline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogenchloride
cis-4-hydroxy-N-triphenylmethyl-L-proline
129431-03-4

cis-4-hydroxy-N-triphenylmethyl-L-proline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With acetic acid for 0.25h; Ambient temperature;1.2 g
cis-L-hydroxyproline methyl ester
81102-38-7

cis-L-hydroxyproline methyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With sodium hydroxide for 2h; Yield given;
(2S,4S)-4-(2-Methoxy-propionyloxy)-pyrrolidine-2-carboxylic acid methyl ester

(2S,4S)-4-(2-Methoxy-propionyloxy)-pyrrolidine-2-carboxylic acid methyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Ambient temperature; Yield given;
1-anilinoformyl-l-b-<4-oxy-proline >

1-anilinoformyl-l-b-<4-oxy-proline >

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With ammonia at 90 - 100℃; im Rohr;
N-tert-butoxycarbonyl-L-cis-4-hydroxyproline
87691-27-8

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-cis-4-hydroxyproline With hydrogenchloride In 1,4-dioxane at 20℃; for 19h;
Stage #2: With TEA In ethanol
(2S,4R)-1-tert-butyl 2-ethyl 4-hydroxypyrrolidine-1,2-dicarboxylate
440678-63-7

(2S,4R)-1-tert-butyl 2-ethyl 4-hydroxypyrrolidine-1,2-dicarboxylate

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1.0M LiOH aq. / ethanol / 2 h / 20 °C
2.1: 2M HCl / dioxane / 19 h / 20 °C
2.2: TEA / ethanol
View Scheme
ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4,5-dihydroxy-2-pentenoate
502442-53-7

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4,5-dihydroxy-2-pentenoate

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 84 percent / DMAP; TEA / CH2Cl2 / 20 °C
2.1: 100 percent / imidazole / dimethylformamide / 20 °C
3.1: 98 percent / 1.5M HCl / ethanol / 2 h / 20 °C
4.1: 61 percent / Ph3P; DEAD / CH2Cl2; toluene / 48 h / 0 °C
5.1: 100 percent / H2 / 5 percent Pd/C / ethanol / 24 h / 20 °C
6.1: 91 percent / TBAF / tetrahydrofuran / 20 °C
7.1: 1.0M LiOH aq. / ethanol / 2 h / 20 °C
8.1: 2M HCl / dioxane / 19 h / 20 °C
8.2: TEA / ethanol
View Scheme
ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4,5-isopropylidenedioxy-2-pentenoate

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4,5-isopropylidenedioxy-2-pentenoate

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 85 percent / 0.5M HCl / ethanol / 20 °C
2.1: 84 percent / DMAP; TEA / CH2Cl2 / 20 °C
3.1: 100 percent / imidazole / dimethylformamide / 20 °C
4.1: 98 percent / 1.5M HCl / ethanol / 2 h / 20 °C
5.1: 61 percent / Ph3P; DEAD / CH2Cl2; toluene / 48 h / 0 °C
6.1: 100 percent / H2 / 5 percent Pd/C / ethanol / 24 h / 20 °C
7.1: 91 percent / TBAF / tetrahydrofuran / 20 °C
8.1: 1.0M LiOH aq. / ethanol / 2 h / 20 °C
9.1: 2M HCl / dioxane / 19 h / 20 °C
9.2: TEA / ethanol
View Scheme
ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-2-pentenoate
502442-56-0

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-2-pentenoate

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 100 percent / imidazole / dimethylformamide / 20 °C
2.1: 98 percent / 1.5M HCl / ethanol / 2 h / 20 °C
3.1: 61 percent / Ph3P; DEAD / CH2Cl2; toluene / 48 h / 0 °C
4.1: 100 percent / H2 / 5 percent Pd/C / ethanol / 24 h / 20 °C
5.1: 91 percent / TBAF / tetrahydrofuran / 20 °C
6.1: 1.0M LiOH aq. / ethanol / 2 h / 20 °C
7.1: 2M HCl / dioxane / 19 h / 20 °C
7.2: TEA / ethanol
View Scheme
(R)-3-Allyl-6-methyl-4-((S)-1-phenyl-ethyl)-morpholine-2,5-dione

(R)-3-Allyl-6-methyl-4-((S)-1-phenyl-ethyl)-morpholine-2,5-dione

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) 1M aq. NaOH, 2.) NaH
2: 80 percent / I2 / tetrahydrofuran; H2O / 2 h / Ambient temperature
3: H2 / Pd(OH)2 / methanol / 5 h / Ambient temperature
4: 1M aq. NaOH / methanol / 2 h / Ambient temperature
View Scheme
2-[((R)-2-Methoxy-propionyl)-((S)-1-phenyl-ethyl)-amino]-pent-4-enoic acid methyl ester

2-[((R)-2-Methoxy-propionyl)-((S)-1-phenyl-ethyl)-amino]-pent-4-enoic acid methyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / I2 / tetrahydrofuran; H2O / 2 h / Ambient temperature
2: H2 / Pd(OH)2 / methanol / 5 h / Ambient temperature
3: 1M aq. NaOH / methanol / 2 h / Ambient temperature
View Scheme
(S)-4-(2-Methoxy-propionyloxy)-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester

(S)-4-(2-Methoxy-propionyloxy)-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd(OH)2 / methanol / 5 h / Ambient temperature
2: 1M aq. NaOH / methanol / 2 h / Ambient temperature
View Scheme
(S)-2-((S)-1-Phenyl-ethylamino)-pent-4-enoic acid amide
177186-30-0

(S)-2-((S)-1-Phenyl-ethylamino)-pent-4-enoic acid amide

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: iodine / tetrahydrofuran; H2O / 0.5 h / Ambient temperature
2: H2 / Pd(OH)2 / ethanol / 5 h / 1861.7 Torr / Ambient temperature
3: 1M NaOH / 2 h
View Scheme
(3S,5S)-5-Iodomethyl-3-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one
176966-58-8

(3S,5S)-5-Iodomethyl-3-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd(OH)2 / ethanol / 5 h / 1861.7 Torr / Ambient temperature
2: 1M NaOH / 2 h
View Scheme
(3S,6R,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione
177186-28-6

(3S,6R,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NH3 / ethanol / 0.5 h / 0 °C
2: iodine / tetrahydrofuran; H2O / 0.5 h / Ambient temperature
3: H2 / Pd(OH)2 / ethanol / 5 h / 1861.7 Torr / Ambient temperature
4: 1M NaOH / 2 h
View Scheme
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate
64187-48-0

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) DCC, CuCl / 1.) dioxane, 45-50 deg C, 48 h, 2.) toluene, reflux, 24 h
2: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C
3: 496 mg / H2 / Pd-C / H2O / 3 h / 25 °C / 2660 Torr
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / toluene / 4 h / 5 - 20 °C
2: sodium hydroxide; water / 3 h / 80 °C
3: hydrogenchloride / water / 1 h / 80 °C
View Scheme
(2S,4S)-N-benzyloxycarbonyl-4-formyloxyproline methyl ester
170159-62-3

(2S,4S)-N-benzyloxycarbonyl-4-formyloxyproline methyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C
2: 496 mg / H2 / Pd-C / H2O / 3 h / 25 °C / 2660 Torr
View Scheme
4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 635 g / aq. NaHCO3 / tetrahydrofuran / 17 h / 25 °C
2: 90 percent / SOCl2 / 17 h / 25 °C
3: 1.) DCC, CuCl / 1.) dioxane, 45-50 deg C, 48 h, 2.) toluene, reflux, 24 h
4: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C
5: 496 mg / H2 / Pd-C / H2O / 3 h / 25 °C / 2660 Torr
View Scheme
Multi-step reaction with 4 steps
1: 86 percent / aqueous NaHCO3 / 3 h / from 0 deg C to r.t.
2: 84 percent / K2CO3 / dimethylformamide / 2 h / 0 °C
3: 1.) EtO2CN=NCOOEt, Ph3P, 2.) aq. NaOH / 1.) HCO2H, THF, from 0 deg C to r.t., 18 h; 2.) 1,4-dioxane, 0 deg C, 0.25 h
4: 68 percent / H2 / Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
2: CrO3
3: NaBH4
4: HBr, AcOH
View Scheme
Multi-step reaction with 5 steps
1: thionyl chloride / 6 h / 15 - 60 °C
2: sodium carbonate / water / 5 h / 10 - 20 °C
3: triethylamine / toluene / 4 h / 5 - 20 °C
4: sodium hydroxide; water / 3 h / 80 °C
5: hydrogenchloride / water / 1 h / 80 °C
View Scheme
(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
13504-85-3

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / SOCl2 / 17 h / 25 °C
2: 1.) DCC, CuCl / 1.) dioxane, 45-50 deg C, 48 h, 2.) toluene, reflux, 24 h
3: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C
4: 496 mg / H2 / Pd-C / H2O / 3 h / 25 °C / 2660 Torr
View Scheme
Multi-step reaction with 3 steps
1: 84 percent / K2CO3 / dimethylformamide / 2 h / 0 °C
2: 1.) EtO2CN=NCOOEt, Ph3P, 2.) aq. NaOH / 1.) HCO2H, THF, from 0 deg C to r.t., 18 h; 2.) 1,4-dioxane, 0 deg C, 0.25 h
3: 68 percent / H2 / Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: CrO3
2: NaBH4
3: HBr, AcOH
View Scheme
N-Benzoyl-2(S)-(2-propenyl)glycin-(1R,2S,5R)-menthylester
157401-61-1

N-Benzoyl-2(S)-(2-propenyl)glycin-(1R,2S,5R)-menthylester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / I2, H2O / tetrahydrofuran / 3 h / 20 °C
2: 100 percent / 2 M aq. HCl / 3 h / 140 °C
View Scheme
N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester
13500-53-3

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) EtO2CN=NCOOEt, Ph3P, 2.) aq. NaOH / 1.) HCO2H, THF, from 0 deg C to r.t., 18 h; 2.) 1,4-dioxane, 0 deg C, 0.25 h
2: 68 percent / H2 / Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature
View Scheme
(S)-2,2-Bis(trifluormethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-on
146197-81-1

(S)-2,2-Bis(trifluormethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-on

hydroxy L-proline
618-27-9

hydroxy L-proline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / 2 / CH2Cl2 / 24 h / Ambient temperature
2: 68 percent / Na(BH3CN), glacial HOAc / propan-2-ol / 1 h / 0 °C
3: 41 percent / H2O / propan-2-ol / Ambient temperature
View Scheme
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

hydroxy L-proline
618-27-9

hydroxy L-proline

(2S,4S)-1-(9H-fluorene-9-ylmethoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
189249-10-3

(2S,4S)-1-(9H-fluorene-9-ylmethoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; Inert atmosphere;100%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃;92%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 9h;
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

hydroxy L-proline
618-27-9

hydroxy L-proline

1-(benzenesulphonyl)-4-hydroxypyrrolidine-2-carboxylic acid
16257-78-6

1-(benzenesulphonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water for 4h;99.99%
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

hydroxy L-proline
618-27-9

hydroxy L-proline

4-hydroxy-1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid

4-hydroxy-1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water for 4h;99.97%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

hydroxy L-proline
618-27-9

hydroxy L-proline

4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid
16257-64-0

4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water for 4h;99.86%
N-methylmaleimide
930-88-1

N-methylmaleimide

hydroxy L-proline
618-27-9

hydroxy L-proline

acenaphthene quinone
82-86-0

acenaphthene quinone

7′-hydroxy-2′-methyl-3a′,6′,7′,8′,8a′,8b′-hexahydro-1′H,2Hspiro[acenaphthylene-1,4′-pyrrolo[3,4-a]pyrrolizine]-1′,2,3′(2′H)-trione

7′-hydroxy-2′-methyl-3a′,6′,7′,8′,8a′,8b′-hexahydro-1′H,2Hspiro[acenaphthylene-1,4′-pyrrolo[3,4-a]pyrrolizine]-1′,2,3′(2′H)-trione

Conditions
ConditionsYield
In methanol at 60℃; for 3h;90%
...Expand
benzyl chloroformate
501-53-1

benzyl chloroformate

hydroxy L-proline
618-27-9

hydroxy L-proline

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline
13504-86-4

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃;84%
With sodium hydrogencarbonate for 3h; from 0 deg C to r.t.;81%
With sodium hydroxide
ethanol
64-17-5

ethanol

hydroxy L-proline
618-27-9

hydroxy L-proline

cis-4-hydroxy-L-prolin-ethyl ester
440678-43-3

cis-4-hydroxy-L-prolin-ethyl ester

Conditions
ConditionsYield
With thionyl chloride at 0℃; for 16h; Reflux;83%
With hydrogenchloride
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

hydroxy L-proline
618-27-9

hydroxy L-proline

1,8-dimethyl-11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline

1,8-dimethyl-11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline

Conditions
ConditionsYield
Montmorillonite K10 In dimethyl sulfoxide microwave irradiation;80%
...Expand
Hexanoyl chloride
142-61-0

Hexanoyl chloride

hydroxy L-proline
618-27-9

hydroxy L-proline

C17H29NO5

C17H29NO5

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water for 4h; Reflux;79%
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

4-methyl-1,2-diaminobenzene
496-72-0

4-methyl-1,2-diaminobenzene

hydroxy L-proline
618-27-9

hydroxy L-proline

8-methyl-11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline

8-methyl-11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline

Conditions
ConditionsYield
Montmorillonite K10 In dimethyl sulfoxide microwave irradiation;78%
...Expand
7-chloro-2-(2-methyl-[1,1'-biphenyl]-3-yl)-2H-indazole-5-carbaldehyde

7-chloro-2-(2-methyl-[1,1'-biphenyl]-3-yl)-2H-indazole-5-carbaldehyde

hydroxy L-proline
618-27-9

hydroxy L-proline

(2S,4S)-1-((7-chloro-2-(2-methyl-[1,1’-biphenyl]-3-yl)-2H-indazol-5-yl)methyl)-4-hydroxypyrrolidine-2-carboxylic acid

(2S,4S)-1-((7-chloro-2-(2-methyl-[1,1’-biphenyl]-3-yl)-2H-indazol-5-yl)methyl)-4-hydroxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 7-chloro-2-(2-methyl-[1,1'-biphenyl]-3-yl)-2H-indazole-5-carbaldehyde; hydroxy L-proline With acetic acid In methanol at 20℃; for 1h;
Stage #2: With sodium cyanoborohydride In methanol at 20℃;		46%
C24H18N4O7
855781-84-9

C24H18N4O7

hydroxy L-proline
618-27-9

hydroxy L-proline

C25H22N4O7

C25H22N4O7

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 24h;39%
4-([1,1′:2′,1″-terphenyl]-3′-ylmethoxy)-3-bromobenzaldehyde

4-([1,1′:2′,1″-terphenyl]-3′-ylmethoxy)-3-bromobenzaldehyde

hydroxy L-proline
618-27-9

hydroxy L-proline

(2S,4S)-1-(4-([1,1′:2′,1″-terphenyl]-3′-ylmethoxy)-3-bromobenzyl)-4-hydroxypyrrolidine-2-carboxylic acid

(2S,4S)-1-(4-([1,1′:2′,1″-terphenyl]-3′-ylmethoxy)-3-bromobenzyl)-4-hydroxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-([1,1′:2′,1″-terphenyl]-3′-ylmethoxy)-3-bromobenzaldehyde; hydroxy L-proline With acetic acid In N,N-dimethyl-formamide at 25℃; for 2h;
Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide for 20h;		37%
6-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)-2-naphthaldehyde

6-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)-2-naphthaldehyde

hydroxy L-proline
618-27-9

hydroxy L-proline

(2S,4S)-1-((6-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)naphthalen-2-yl)methyl)-4-hydroxypyrrolidine-2-carboxylic acid

(2S,4S)-1-((6-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)naphthalen-2-yl)methyl)-4-hydroxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 60℃; for 12h;20%
1-benzyl-1H-pyrrole-2,5-dione
1631-26-1

1-benzyl-1H-pyrrole-2,5-dione

β-naphthaldehyde
66-99-9

β-naphthaldehyde

hydroxy L-proline
618-27-9

hydroxy L-proline

(-)-(3aR,4S,7R,8aR,8bS)-hexahydro-7-hydroxy-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione
935468-53-4

(-)-(3aR,4S,7R,8aR,8bS)-hexahydro-7-hydroxy-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 85℃; for 20h;17%
...Expand
6-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)-2-naphthaldehyde

6-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)-2-naphthaldehyde

hydroxy L-proline
618-27-9

hydroxy L-proline

(2S,4S)-4-hydroxy-1-((6-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)naphthalen-2-yl)methyl)pyrrolidine-2-carboxylic acid

(2S,4S)-4-hydroxy-1-((6-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)naphthalen-2-yl)methyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 60℃; for 12h;15%

cis-4-Hydroxy-L-proline Specification

The Hydroxyproline cis-form, with the CAS registry number 618-27-9, is also known as (4S)-4-Hydroxy-L-prolin. It belongs to the product categories of Pyrrole & Pyrrolidine & Pyrroline; Chiral Reagent; Amino Acids; Biochemistry; Biological-Modified Amino Acids; Chiral Compound; Amino Acids & Derivatives; Chiral Reagents; Heterocycles. Its EINECS registry number is 210-542-1. This chemical's molecular formula is C5H9NO3 and molecular weight is 131.13. What's more, its IUPAC name is called (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid. It should be stored in a cool, dry place. This chemical can be prepared by gelatin, bone glue product, delibakery product. The reaction needs hydrolyzing with hydrochloric acid and purification, crystallization. It is used as the taste agent, nutritional fortifiers or fragrance materials.

Physical properties about Hydroxyproline cis-form are: (1)ACD/LogP: -1.84; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4 ; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 38.77 Å2; (11)Index of Refraction: 1.54; (12)Molar Refractivity: 29.49 cm3; (13)Molar Volume: 93.9 cm3; (14)Surface Tension: 62.2 dyne/cm; (15)Density: 1.395 g/cm3; (16)Flash Point: 168.6 °C; (17)Enthalpy of Vaporization: 69.51 kJ/mol; (18)Boiling Point: 355.2 °C at 760 mmHg; (19)Vapour Pressure: 1.8E-06 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should avoid contacting with skin, eyes and wear suitable protective clothing, gloves. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)[C@H]1NC[C@@H](O)C1
(2) InChI: InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
(3) InChIKey: PMMYEEVYMWASQN-IMJSIDKUSA-N

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