Basic information
- CAS
33996-33-7- Standard SMILES
CC(=O)N1C[C@H](O)C[C@H]1C(=O)O- InChIKey
BAPRUDZDYCKSOQ-RITPCOANSA-N- Molecular formula
- C7H11NO4
- Average molar mass
- 173.17 g/mol
- Monoisotopic mass
- 173.06880783
Overview
Oxaceprol is an L-proline derivative that is L-proline substituted by acetyl and hydroxy groups at positions 1 and 4R, respectively. It is an anti-inflammatory drug used for the management of osteoarthritis. It has a role as an anti-inflammatory drug and a dermatologic drug. It is a member of acetamides, a pyrrolidinemonocarboxylic acid, a monohydroxypyrrolidine and a L-proline derivative.
Names & identifiers
- Preferred name
- Oxaceprol
- IUPAC
- (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid
- English name
- Oxaceprol
- Molecular formula
- C7H11NO4
- Molecular weight
- 173.17
Names & synonyms
Oxaceprol33996-33-7(2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acidJonctumacetyl hydroxyprolineOxaceprolumN-AcetylhydroxyprolineDTXSID2046410Q0XV76B96L(-)-1-Acetyl-4-hydroxy-L-prolineDTXCID0026410RefChem:55788
Show more names
(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACIDNAHPTRANS-1-ACETYL-4-HYDROXY-L-PROLINECO-61AHP-200Ac-L-Hyp
1-Acetyl-4-hydroxy-L-prolineD11AX09M01AX24251-780-6N-acetyl-4-hydroxyprolineN-Acetyl-L-hydroxyprolineAC-HYP-OHN-Acetyl-trans-4-hydroxy-L-proline
Database identifiers
- CAS
33996-33-7- PubChem CID
- 65784
- DTXSID
DTXSID2046410- ChEMBL
CHEMBL1407356- ChEBI
CHEBI:233149- UNII
- Q0XV76B96L
- EC Number
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 215
Experimental & physicochemical properties
Solubility>26 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- Melting point
- 132 · 132-133 °C (dec.)(lit.)
- alpha
- -119 · -119 º (c=4 in H2O)
- Boiling point
- 303.8 °C · 303.8°C (rough estimate)
- Density
- 1.3346 · 1.3346 (rough estimate)
- vapor pressure
- 0 Pa · 0Pa at 20℃
- refractive index
- 1.449 · 1.4490 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 32 mg/mL · DMSO : ≥ 32 mg/mL (184.79 mM)
- pka
- 3.48 · 3.48±0.40(Predicted)
- form
- Crystalline Powder
- color
- White
- optical activity
- 20 · [α]20/D 119°, c = 4 in H2O
- Merck
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (11.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 28-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21835
Hazard Classes and CategoriesSkin Irrit. 2 (11.8%)
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339900
- risk_code
- 41
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H318
- REACH Registrations
- Inactive
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
M - Musculo-skeletal system
QD - Dermatologicals
QM - Musculo-skeletal system
MeSH Pharmacological Classification
Drugs used to treat or prevent skin disorders or for the routine care of skin.
Drugs that are used to treat RHEUMATOID ARTHRITIS.
Uses & manufacturing
General Manufacturing InformationL-Proline, 1-acetyl-4-hydroxy-, (4R)-: INACTIVE
Applications
Usestrans-1-Acetyl-4-hydroxy-L-proline can be used:In the stereospecific synthesis of 4-fluoroglutamic acid.To synthesize molecular targets for von Hippel-Lindau (VHL) E3 ubiquitin ligase.As a precursor to synthesize pseudopoly(amino acids) such as poly(trans-4-hydroxy-4-acyl-L-proline ester) and a biodegradable polymer, poly(lactic acid-glycolic acid-4-hydroxyproline).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
2 records
Compound notes
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