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Basic Information
CAS No.: 33996-33-7
Name: Oxaceprol
Article Data: 7
Molecular Structure:
Molecular Structure of 33996-33-7 (Oxaceprol)
Formula: C7H11NO4
Molecular Weight: 173.169
Synonyms: L-Proline,1-acetyl-4-hydroxy-, trans-;Proline, 1-acetyl-4-hydroxy-, L- (7CI,8CI);(R)-N-Acetyl-4-hydroxy-L-proline;AHP 200;CO 61;Jonctum;N-Acetyl-4-hydroxy-L-proline;N-Acetyl-trans-4-hydroxy-L-proline;N-Acetylhydroxyproline;Oxaceprol;trans-N-Acetyl-4-hydroxy-L-proline;L-Proline,1-acetyl-4-hydroxy-, (4R)-;
EINECS: 251-780-6
Density: 1.439 g/cm3
Melting Point: 132-133 °C (dec.)(lit.)
Boiling Point: 442.1 °C at 760 mmHg
Flash Point: 221.2 °C
Appearance: White fine crystals
Hazard Symbols: IrritantXi
Risk Codes: 41
Safety: 26-36
PSA: 77.84000
LogP: -1.00940
Synthetic route
108-24-7

acetic anhydride

51-35-4

4R-4-hydroxyproline

33996-33-7

oxaceprol

Conditions
ConditionsYield
In water at 40 - 50℃; for 3h;70%
With acetic acid
In dichloromethane
43176-83-6

(2S,4R)-N-acetyl-4-benzoyloxy-proline

33996-33-7

oxaceprol

Conditions
ConditionsYield
With sodium hydroxide
51-35-4

4R-4-hydroxyproline

33996-33-7

oxaceprol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NaOH / 0 °C / anschliessend Behandeln mit Benzoylchlorid
2: aqueous NaOH
View Scheme
64-17-5

ethanol

33996-33-7

oxaceprol

33996-28-0

(2S,4R)-1-acetyl-4-hydroxyproline ethyl ester

Conditions
ConditionsYield
With acetyl chloride Reflux;99%
33996-33-7

oxaceprol

72485-25-7

(1S,4S)-5-acetyl-2-oxa-5-azabicyclo<2.2.1>heptan-3-one

Conditions
ConditionsYield
90%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature;70%
18162-48-6

tert-butyldimethylsilyl chloride

33996-33-7

oxaceprol

130680-40-9

(4R)-1-Acetyl-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-L-proline

Conditions
ConditionsYield
Stage #1: tert-butyldimethylsilyl chloride; oxaceprol With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃;
Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 1.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; water pH=3;
84%
Stage #1: tert-butyldimethylsilyl chloride; oxaceprol With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 10℃; for 1h;
Stage #2: With water In acetonitrile for 0.416667h;
33996-33-7

oxaceprol

444313-67-1

(1R,4R)-5-acetyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one

Conditions
ConditionsYield
With acetic anhydride at 90℃; for 7h;82%
With acetic anhydride at 20 - 90℃; for 71h; Inert atmosphere;45%
98-88-4

benzoyl chloride

33996-33-7

oxaceprol

43176-83-6

(2S,4R)-N-acetyl-4-benzoyloxy-proline

Conditions
ConditionsYield
With pyridine for 2h; Ambient temperature;75%
67-56-1

methanol

33996-33-7

oxaceprol

67943-19-5

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

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;66%
With thionyl chloride at 0℃; Reflux;29%
100-46-9

benzylamine

33996-33-7

oxaceprol

(2S,4R)-1-acetyl-N-benzyl-4-hydroxypyrrolidine-2-carboxamide

Conditions
ConditionsYield
With tris(2,2,2-trifluoroethyl) borate at 100℃; under 760.051 Torr; for 5h;50%
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    Ac-Hyp-OH

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Specification

1. Introduction of N-Acetyl-L-hydroxyproline

N-Acetyl-L-hydroxyproline, with the IUPAC name of (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid, is one kind of powder. The product's categories are Pyrrole; API Intermediates; Amino Acids; Hydroxyproline [Hyp]; Peptide Synthesis; Proline Derivatives; Unnatural Amino Acid Derivatives. It is white crystalline powder which is soluble in water. And AC-HYP-OH is an anti-inflammatory drug used in the treatment of osteoarthritis. Additionally, it should be sealed in the container and stored at the normal temperature.

2. Properties of N-Acetyl-L-hydroxyproline

The other characteristics of AC-HYP-OH can be summarized as: (1)ACD/LogP: -2.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.33; (4)ACD/LogD (pH 7.4): -5.66; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.56; (13)Molar Refractivity: 38.91 cm3; (14)Molar Volume: 120.2 cm3; (15)Polarizability: 15.42×10-24 cm3; (16)Surface Tension: 69.6 dyne/cm; (17)Enthalpy of Vaporization: 80.74 kJ/mol; (18)Vapour Pressure: 1.13E-09 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 173.068808; (21)MonoIsotopic Mass: 173.068808; (22)Topological Polar Surface Area: 77.8; (23)Heavy Atom Count: 12; (24)Complexity: 216.

3. Structure Descriptors of N-Acetyl-L-hydroxyproline

You could convert the following datas into the molecular structure:
1. SMILES:O=C(N1[C@H](C(=O)O)C[C@@H](O)C1)C
2. InChI:InChI=1/C7H11NO4/c1-4(9)8-3-5(10)2-6(8)7(11)12/h5-6,10H,2-3H2,1H3,(H,11,12)/t5-,6+/m1/s1 
3. InChIKey:BAPRUDZDYCKSOQ-RITPCOANBI

4. Safety Information of N-Acetyl-L-hydroxyproline

Hazard Codes: Xi
Risk Statements: 41
Safety Statements: 26-36
WGK Germany: 3
F: 10

When you are using this chemical, please be cautious about it as the following:
It may cause serious damage to the eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.