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147-85-3 molecular structure
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(2S)-pyrrolidine-2-carboxylic acid

ChemBase ID: 57
Molecular Formular: C5H9NO2
Molecular Mass: 115.13046
Monoisotopic Mass: 115.06332853
SMILES and InChIs

SMILES:
OC(=O)[C@H]1NCCC1
Canonical SMILES:
OC(=O)[C@@H]1CCCN1
InChI:
InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
InChIKey:
ONIBWKKTOPOVIA-BYPYZUCNSA-N

Cite this record

CBID:57 http://www.chembase.cn/molecule-57.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-pyrrolidine-2-carboxylic acid
IUPAC Traditional name
L-proline
Synonyms
2-Pyrrolidinecarboxylic acid
(S)-Proline
(S)-2-Pyrrolidinecarboxylic acid
(S)-2-Carboxypyrrolidine
(-)-Proline
(-)-2-Pyrrolidinecarboxylic acid
L-Proline
2-Pyrrolidine carboxylic acid
L-PROLINE, U.S.P.
(S)-Pyrrolidine-2-carboxylic acid
L-Proline
L-(-)-proline
(2S)-pyrrolidine-2-carboxylic acid
2-Pyrrolidinecarboxylic acid
L-Proline
H-Pro-OH
Proline
(S)-吡咯烷-2-羧酸
L-脯氨酸
CAS Number
147-85-3
EC Number
205-702-2
MDL Number
MFCD00064318
Beilstein Number
80810
Merck Index
147780
PubChem SID
160963520
24887885
46506858
24887886
24898097
24901637
24898677
24898986
PubChem CID
145742
FEMA ID
3318
Council of Europe Number
10378
Flavis Number
17.019

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.9406707  H Acceptors
H Donor LogD (pH = 5.5) -2.5687168 
LogD (pH = 7.4) -2.5686643  Log P -2.5686383 
Molar Refractivity 28.0643 cm3 Polarizability 11.294152 Å3
Polar Surface Area 49.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.71  LOG S 0.5 
Solubility (Water) 3.65e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble50 mg/mL expand Show data source
Soluble expand Show data source
Apperance
powder expand Show data source
Powder expand Show data source
Melting Point
220-222°C expand Show data source
228 °C (dec.)(lit.) expand Show data source
ca 225°C dec. expand Show data source
Density
1.36 expand Show data source
Optical Rotation
[α]20/D -84.5±1°, c = 5% in H2O expand Show data source
[α]20/D -84°, c = 4 in H2O expand Show data source
[α]20/D -85.0±1.0°, c = 5% in H2O expand Show data source
-84 (c=1 in water) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 0.05 expand Show data source
λ: 280 nm Amax: 0.05 expand Show data source
Hydrophobicity(logP)
-2.4 expand Show data source
-2.413 expand Show data source
pH
6.0-7.0 (20 °C, 1 M in H2O) expand Show data source
6.0-7.0 (25 °C, 1 M in H2O) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Storage Warning
Hygroscopic expand Show data source
IRRITANT expand Show data source
RTECS
TW3584000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
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Download expand Show data source
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Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Regulation Compliance
FCC expand Show data source
FDA 21 CFR (172.320) expand Show data source
Purity
≥99% expand Show data source
>99% (TLC) expand Show data source
≥98.5% expand Show data source
≥99% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% expand Show data source
≥99.0% (NT) expand Show data source
≥99.5% (NT) expand Show data source
95% expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
Halal expand Show data source
Kosher expand Show data source
NI expand Show data source
ReagentPlus® expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Optical Purity
ee: 98% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
<0.1% expand Show data source
≤0.1% expand Show data source
≤0.1% (as SO4) expand Show data source
Impurities
<0.0005% Phosphorus (P) expand Show data source
<0.1% Insoluble matter expand Show data source
≤0.3% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
L-Hydroxyproline, free expand Show data source
Cation Traces
Al: <0.0005% expand Show data source
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: <0.0005% expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: <0.0005% expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: <0.0005% expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: <0.005% expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: <0.0005% expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: <0.005% expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: <0.05% expand Show data source
NH4+: ≤20 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: <0.001% expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: <0.0005% expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): <0.05% expand Show data source
chloride (Cl-): ≤100 mg/kg expand Show data source
sulfate (SO42-): <0.05% expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.1% loss on drying, 20 °C (HV) expand Show data source
≤0.2% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
1 M in H2O expand Show data source
Product Line
BioUltra expand Show data source
BioXtra expand Show data source
abs.
A1M/260, H2O <0.05 expand Show data source
A1M/280, H2O <0.05 expand Show data source
Empirical Formula (Hill Notation)
C5H9NO2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals
DrugBank - DB00172 external link
Item Information
Drug Groups approved; nutraceutical
Description A non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. [PubChem]
Indication L-Proline is extremely important for the proper functioning of joints and tendons and also helps maintain and strengthen heart muscles.
Pharmacology L-Proline is a major amino acid found in cartilage and is important for maintaining youthful skin as well as repair of muscle, connective tissue and skin damage. It is also essential for the immune system, and for necessary balance of this formula. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is extremely important for the proper functioning of joints and tendons. Helps maintain and strengthen heart muscles.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
External Links
Wikipedia
Sigma Aldrich - W331902 external link
Packaging
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum
Sigma Aldrich - 81710 external link
Other Notes
Proline-catalyzed asymmetric Robinson annelation1; Asymmetric self-condensation of β-ionylideneacetaldehyde, retinal and related compounds2
Sigma Aldrich - 81709 external link
Other Notes
Protects enzymes against heat inactivation1; Growth requirement of various microorganisms2
Sigma Aldrich - 93693 external link
Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 131547 external link
Application
Catalyst for enantioselective reduction of ketones.1 Ligand used in TLC resolution of amino acids.2 Synthon for dolaproine and related diastereomers.3
Sigma Aldrich - P8865 external link
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - P0380 external link
Packaging
1 kg in poly bottle
10 mg in autosmp vl
100 g in poly bottle
5 kg in poly drum
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC
MP Biomedicals - 02199543 external link
Solid
MP Biomedicals - 02194728 external link
Cell Culture Reagent
Crystalline
Purity: 99+%
Hydroxy-L -proline free
MP Biomedicals - 02102730 external link
Crystalline
Purity: 99+%
Hydroxy-L-proline free
MP Biomedicals - 05217149 external link
MP Biomedicals Rare Chemical collection

REFERENCES

REFERENCES

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  • • For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methylcyclopentane-1,3-dione, A13936. For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl azodicarboxylate, L19347: J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl azodicarboxylate, L19348: Angew. Chem. Int. Ed., 41, 1790 (2002).
  • • For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).
  • • For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).
  • • For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethylacetaldehyde, A15013.
  • • The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑ?-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).
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PATENTS

PATENTS

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