Basic information
- Standard SMILES
O=C(O)[C@@H]1C[C@@H](O)CN1- InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N- Molecular formula
- C5H9NO3
- Average molar mass
- 131.13 g/mol
- Monoisotopic mass
- 131.05824315
Overview
Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline having L-trans-configuration. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is a tautomer of a trans-4-hydroxy-L-proline zwitterion.
Names & identifiers
- Preferred name
- L-Hydroxyproline
- IUPAC
- (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
- English name
- L-Hydroxyproline
- Molecular formula
- C5H9NO3
- Molecular weight
- 131.13
Names & synonyms
L-Hydroxyproline51-35-4trans-4-Hydroxy-L-prolinehydroxyprolineHyprohydroxy-L-proline(4R)-4-hydroxy-L-prolinetrans-L-HydroxyprolineL-Proline, 4-hydroxy-, (4R)-trans-Hydroxyproline4-Hydroxy-2-pyrrolidinecarboxylic aciddelta-Hydroxyproline
Show more names
Hyp(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID4-HYDROXY-L-PROLINE4-HydroxyprolineH-HYP-OH4R-4-hydroxyproline4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID5kg
L-Proline, 4-hydroxy-, trans-(2S,4R)-4-hydroxyprolineRMB44WO89XLUMISTORL-threo-4-hydroxyprolineNSC-46704(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acidCHEBI:18095
Database identifiers
- CAS
51-35-4、618-28-0- PubChem CID
- 5810
- DTXSID
DTXSID10883225- ChEMBL
CHEMBL352418- ChEBI
CHEBI:18095- UNII
- RMB44WO89X
- EC Number
- 200-091-9
- Nikkaji
- J148.015D
Properties
Computed structural properties
- XLogP
- -3.3
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 125
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning; Surfactant; Antistatic; Hair conditioning
LogP-3.17
Food AdditivesUse unspecified -> FDA Substance added to food
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 Description
Solid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]
Solid
Dissociation ConstantspK1′ 1.82 and pK2′ 9.65
Collision Cross Section
130.23 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
139.3 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
122 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
128.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
127.9 Ų [M+H]+
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)
- refractive index
- -75.5 ° · -75.5 ° (C=4, H2O)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- Crystals or Crystalline Powder
- pka
- 1.82 · 1.82, 9.66(at 25℃)
- color
- White
- Odor
- Odorless
- PH
- 5.5 · 5.5-6.5 (50g/l, H2O, 20℃)
- optical activity
- 25 · [α]25/D 75.6°, c = 1 in H2O
- Water Solubility
- 357.8 g/L · 357.8 g/L (20 º C)
- Merck
- 14 · 14,4840
- BRN
- 471933 · 471933
- Cosmetics Ingredients Functions
- HAIR CONDITIONINGANTISTATICSURFACTANT - CLEANSINGSKIN CONDITIONING
- InChI
- 1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
- InChIKey
- PMMYEEVYMWASQN-DMTCNVIQSA-N
- SMILES
- O[C@H]1CN[C@@H](C1)C(O)=O
- LogP
- -0.35 · -0.350 (est)
- CAS DataBase Reference
- 51 · 51-35-4(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- L-HYDROXYPROLINE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 44 WO89X · RMB44WO89X
- NIST Chemistry Reference
- Hydroxyproline(51-35-4)
- EPA Substance Registry System
- -4 · trans-4-Hydroxy-L-proline (51-35-4)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P271-P280
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-22
- Safety Statements
- 24 · 24/25-36/37/39-27-26
- WGK Germany
- 3 · 3
- RTECS
- 3586500 · TW3586500
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29339990 · 29339990
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 89.3% (25 of 28) of all reports.
Warning
H315 (10.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 28 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: L-Proline, 4-hydroxy-, (4R)-
Status: Active Update: 27-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21207
L-Proline, 4-hydroxy-, (4R)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - L-Proline, 4-hydroxy-, trans-: Environment tier I assessment
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See L-Proline.
Hazard Classes and CategoriesSkin Irrit. 2 (10.7%)
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
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)
Uses & manufacturing
Uses
An analog of proline and an non-essential amino acid found in collagen; [Merck Index]
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Use ClassificationCosmetics -> Skin conditioning; Surfactant; Antistatic; Hair conditioning
General Manufacturing InformationL-Proline, 4-hydroxy-, (4R)-: ACTIVE
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
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: An optically active form of 4-hydroxyproline having L-trans-configuration.
Related reactions
448 records
Linked notes
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