trans-hydroxy-L-proline
Basic information
- CAS
51-35-4- Standard SMILES
O=C([O-])[C@@H]1C[C@@H](O)C[NH2+]1- InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N- Molecular formula
- C5H9NO3
- Average molar mass
- 131.13 g/mol
- Monoisotopic mass
- 131.05824315
Overview
Trans-4-hydroxy-L-proline zwitterion is an L-alpha-amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of trans-4-hydroxy-L-proline; major species at pH 7.3. It is a tautomer of a trans-4-hydroxy-L-proline.
Names & identifiers
- Preferred name
- trans-hydroxy-L-proline
- IUPAC
- (2S,4R)-4-hydroxypyrrolidin-1-ium-2-carboxylate
- English name
- L-Hydroxyproline
- Molecular formula
- C5H9NO3
- Molecular weight
- 131.13
Names & synonyms
trans-oxyprolinetrans-hydroxy-L-prolinehydroxyproline zwitteriontrans-L-4-hydroxy-prolineCHEBI:58375trans-4-hydroxy-L-proline zwitterionHypTRANS-4-HYDROXY-L-PROLINEHYDROXYPROLINE(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID4-HYDROXY-L-PROLINE4-Hydroxyproline
Show more names
H-HYP-OH4R-4-hydroxyproline4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID5kg
Database identifiers
- CAS
51-35-4、618-28-0- PubChem CID
- 6971053
- ChEBI
CHEBI:58375
Properties
Computed structural properties
- XLogP
- -2.7
- Topological polar surface area
- 77 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 120
Experimental & physicochemical properties
LogP-3.17
Solubility
Soluble in water at 0, 25, 50, and 60 °C
361 mg/mL at 25 °C
Boiling PointDecomposes
Melting Point
274°C
274 - 275 °C
Physical DescriptionSolid
Dissociation ConstantspK1′ 1.82 and pK2′ 9.65
Physicochemical properties
- Melting point
- 273 °C · 273 °C (dec.)(lit.)
- alpha
- -75.5 · -75.5 º (c=5, H2O)
- Boiling point
- 242.42 °C · 242.42°C (rough estimate)
- Density
- 1.3121 · 1.3121 (rough estimate)
- bulk density
- 610 kg/m3 · 610kg/m3
- vapor density
- 4.5 · 4.5 (vs air)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TW3586500
- hs_code
- 29339990
- risk_code
- 36/37/38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 24/25-36/37/39-27-26
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Pharmacology
Pharmacodynamics
Hydroxyproline as well as proline and glycine are the major components of collagen. Collagen is on one of the main building blocks of connective tissue such as skin, bone, and cartilage. Thus when these tissues are damaged, hydroxyproline is necessary for repair of the damaged area.
Tissue LocationsEpidermis
Cellular LocationsEndoplasmic reticulum
Metabolite PathwaysArginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Applications
DescriptionA non-essential amino acid. Can be isolated from gelatin. Hydroxyproline has not been reported as added to food in any of the NAS surveys.
UsesA versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins.
Useshydroxyproline is a skin-conditioning amino acid. It is a component of collagen.
UsesA natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.
General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Upstream & downstream products
Upstream raw materials
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