DL-Hydroxyproline
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DL-Hydroxyproline
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CAS No:
618-28-0
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Formula:
C5H9NO3
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Chemical Name:
DL-Hydroxyproline
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Synonyms:
D-Proline,4-hydroxy-,(4S)-rel-;Proline,4-hydroxy-,DL-;DL-Proline,4-hydroxy-,trans-;rel-(4S)-4-Hydroxy-D-proline;DL-Hypro;trans-DL-Hydroxyproline;DL-Hydroxyproline;(±)-Hydroxyproline;trans-4-Hydroxy-DL-proline;22775-69-5
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CAS No:
Description
Solid
Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline having L-trans-configuration. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is a tautomer of a trans-4-hydroxy-L-proline zwitterion.|Hydroxyproline is a neutral heterocyclic protein amino acid. It is found in collagen and as such it is common in many gelatin products. Hydroxyproline is mostly used as a diagnostic marker of bone turnover and liver fibrosis. Therapeutically, hydroxyproline is being studied as an an experimental medicine but is approved in France as a combination topical gel product called Cicactive for small, superficial wounds.
Characteristics
69.6 Ų
-3.17
248-250 °C
Decomposes
Soluble in water at 0, 25, 50, and 60 °C|361 mg/mL at 25 °C
pK1′ 1.82 and pK2′ 9.65
128.1 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|130.23 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|122 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|127.9 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|139.3 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|126.2 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|126.3 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|126.7 Ų [M-H]-
Drug Information
Used in France as a combination product for the treatment of small, superficial wounds.
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.
N-methyl-trans-4-hydroxy-L-proline
DL-Hydroxyproline Use and Manufacturing
L-Proline, 4-hydroxy-, (4R)-: ACTIVE
Cosmetics -> Antistatic; Hair conditioning; Skin conditioning; Surfactant
Computed Properties
Molecular Weight:131.13
XLogP3:-3.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:131.058243149
Monoisotopic Mass:131.058243149
Topological Polar Surface Area:69.6
Heavy Atom Count:9
Complexity:125
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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