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CAS No 51-35-4 , (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

  • Name: (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
  • Synonyms: trans-L-Hydroxyproline; L-4-hydroxyproline;L-Hydroxyproline; Hypro; trans-Hydroxyproline; hydroxyproline;(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid; hydroxy-L-proline; trans-4-Hydroxy-L-proline;
  • CAS Registry Number:
  • Melting Point: 274-275 ºC
  • Flash Point: 168.6 ºC
  • Boiling Point: 355.2 ºC at 760 mmHg
  • Density: 1.395 g/cm3
  • Refractive index: -75.5 ° (C=4, H2O)
  • Alpha: -75.5 º (C=5, H2O)
  • Water Solubility: 357.8 G/L (20 º C)
  • Safety Statements: 36/37/38,
  • Hazard Symbols: Xi:;
  • HS Code: 29339990
  • Flash Point: 168.6 ºC
  • EINECS: 200-091-9
  • Molecular Weight: 131.12986
  • InchiKey: PMMYEEVYMWASQN-DMTCNVIQSA-N
  • InChI: 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
  • Risk Statements: S24/25
  • Molecular Formula: C5H9NO3
  • Molecular Structure:CAS No:51-35-4 (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

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References of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
Title: Hydroxyproline
CAS Registry Number: 51-35-4
CAS Name: (4R)-4-Hydroxy-L-proline
Synonyms: Hyp; Ls-hydroxyproline; (-)-(2S,4R)-4-hydroxyproline; trans-4-hydroxyproline; 4(R)-hydroxy-2(S)-pyrrolidinecarboxylic acid
Molecular Formula: C5H9NO3
Molecular Weight: 131.13
Percent Composition: C 45.80%, H 6.92%, N 10.68%, O 36.60%
Literature References: Amino acid analog of proline, q.v.; non-essential for human development. Shows cis-trans isomerism. Constituent of collagen, q.v. Isoln from gelatin: E. Fischer, Ber. 35, 2660 (1902). Synthesis: H. Leuchs, Ber. 38, 1937 (1905); and structure determn: H. Leuchs, J. F. Brewster, Ber. 46, 986 (1913). Stereochemistry: Hudson, Neuberger, J. Org. Chem. 15, 24 (1950). Early chemistry and biochemistry: Amino Acids and Proteins, D. M. Greenberg, Ed. (Charles C. Thomas, Springfield, IL, 1951) 950 pp., passim; J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids vols 1-3 (John Wiley and Sons, Inc., New York, 1961) pp. 2018-2042, passim. Flow sheets of four different syntheses: Chem. Eng. News 40, 40 (Nov. 12, 1962). One pot synthesis: S. G. Ramaswamy, E. Adams, J. Org. Chem. 42, 3440 (1977). Proof of occurence in plants: D. Ashford, A. Neuberger, Trends Biochem. Sci. 5, 245 (1980). Effects of cis-trans isomerism on protein structure: N. Panasik, Jr. et al., Int. J. Pept. Protein Res. 44, 262 (1994). Review: R. Kuttan, A. N. Radhakrishnan, Adv. Enzymol. 37, 273-348 (1973). Review of metabolism: E. Adams, L. Frank, Annu. Rev. Biochem. 49, 1005-1061 (1980).
Properties: Rhombs or needles from water, mp 274°. [a]D -76.5° (c = 2.5 in water). pK1￠ 1.82; pK2￠ 9.65. Soly in water at 0°: 288.6 g/l; at 25°: 361.1 g/l; at 50°: 451.8 g/l; at 65°: 516.7 g/l. Very slightly sol in alcohol. Insol in ether.
Melting point: mp 274°
pKa: pK1￠ 1.82; pK2￠ 9.65
Optical Rotation: [a]D -76.5° (c = 2.5 in water)
 
Derivative Type: cis-Form
CAS Registry Number: 618-27-9
Synonyms: Allohydroxyproline; (2S,4S)-4-hydroxyproline
Properties: mp 238-241°. [a]D18 -58.1° (c = 5.2 in water).
Melting point: mp 238-241°
Optical Rotation: [a]D18 -58.1° (c = 5.2 in water)