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cis-4-Hydroxy-L-proline

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Name

cis-4-Hydroxy-L-proline

EINECS 210-542-1
CAS No. 618-27-9 Density 1.395 g/cm3
PSA 69.56000 LogP -0.87740
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 N/A 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;

Article Data 25

cis-4-Hydroxy-L-proline Synthetic route

157401-62-2

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

618-27-9

hydroxy L-proline

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

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
13504-86-4

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

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
132592-07-5

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

618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 2h; Ambient temperature;68%
148429-59-8

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

618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With water In isopropyl alcohol Ambient temperature;41%
66267-44-5

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

618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogenchloride
19887-35-5, 118712-71-3

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

618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With hydrogenchloride
129431-03-4

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

618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With acetic acid for 0.25h; Ambient temperature;1.2 g
81102-38-7

cis-L-hydroxyproline methyl ester

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

618-27-9

hydroxy L-proline

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Ambient temperature; Yield given;

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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