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(2S)-pyrrolidinium-2-carboxylate

HCID 6971047
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
147-85-3
Standard SMILES
O=C([O-])[C@@H]1CCC[NH2+]1
InChIKey
ONIBWKKTOPOVIA-BYPYZUCNSA-N
Molecular formula
C5H9NO2
Average molar mass
115.13 g/mol
Monoisotopic mass
115.06332853

Overview

L-proline zwitterion is the zwitterion formed from L-proline by proton transfer from the carboxy group to the ring nitrogen. It is the predominant species at physiological pH. It is a tautomer of a L-proline.

Names & identifiers

Preferred name
(2S)-pyrrolidinium-2-carboxylate
IUPAC
(2S)-pyrrolidin-1-ium-2-carboxylate
English name
L-Proline
Molecular formula
C5H9NO2
Molecular weight
115.13

Names & synonyms

prolL-proline zwitterion3ip6CHEBI:60039(2S)-pyrrolidinium-2-carboxylatePROH-PRO-OHL-PROl-prolinL-Pro-OH2-pyrrolidinecarboxylic acid(S)-PYRROLIDINE-2-CARBOXYLIC ACID
Show more names
(2S)-pyrrolidine-2-carboxylic acidL-PolineH-L-PRO-OH

Database identifiers

CAS
147-85-3、4305-67-3
PubChem CID
6971047
ChEBI
CHEBI:60039

Properties

Computed structural properties

XLogP
-1.9
Topological polar surface area
56.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8
Formal charge
0
Complexity
97.1

Experimental & physicochemical properties

LogP-2.54
Solubility162.0 mg/mL
Melting Point221 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
228 °C · 228 °C (dec.) (lit.)
alpha
-85.5 · -85.5 º (c=4, H2O)
Boiling point
215.41 °C · 215.41°C (rough estimate)
bulk density
500 kg/m3 · 500kg/m3
Density
1.35 · 1.35
vapor pressure
0 Pa · 0Pa at 25℃
FEMA
3319 · 3319 | L-PROLINE
refractive index
-85 ° · -85 ° (C=4, H2O)
FLAVIS Number
17.019 · 17.019 | L-Proline
storage temp.

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

F
3-10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
TW3584000
hs_code
29339990
Toxicity
LD50 orally in Rabbit: > 5110 mg/kg
risk_code
36/37/38-22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
24/25-36/37/39-26
Storage Class
13 - Non Combustible Solids
Hazard statements
H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P271-P280
Hazardous Substances Data
147-85-3(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

Glycogenic, by L-Proline oxidase in the kidney, it is ring-opened and is oxidized to form L-Glutamic acid. L-Ornithine and L-Glutamic acid are converted to L-Proline via L-Glutamic acid-gamma-semialdehyde. It is contained abundantly in collagen, and is intimately involved in the function of arthrosis and chordae.

Metabolism/MetabolitesHepatic
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite PathwaysAmikacin Action Pathway
Applications · 4 items

OccurrenceReported found as a component in many proteins; also widely occurring as the free acid in natural products. A major constituent of collagen, the main fibrous protein found in bone, cartilage and other connective tissue.

UsesL-Proline is used as asymmetric catalysts in organic synthesis and asymmetric aldol cyclization. It is involved in the Michael addition of dimethyl malonate to alfa-beta-unsaturated aldehydes. It is a precursor of hydroxyproline in collagen. It is an active component of collagen and involved in the proper functioning of joints and tendons. It finds uses in pharmaceutical, biotechnological applications due to its osmoprotectant property. Further, it is used with ninhydrin in the chromatography.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
2 · 2-8°C
solubility
2 O: · H2O: 50 mg/mL
form
powder
pka
1.95 · 1.95, 10.64(at 25℃)
color
White
PH
6 · 6.0-7.0 (25℃, 1M in H2O)
Odor
100 % · at 100.00 %. odorless
Odor Type
odorless
biological source
synthetic
optical activity
20 · [α]20/D 85.0±1.0°, c = 5% in H2O
Water Solubility
soluble
Sensitive
Hygroscopic
λmax
260 nm · λ: 260 nm Amax: 0.05λ: 280 nm Amax: 0.05
JECFA Number
1425 · 1425
Merck
14 · 14,7780
BRN
80810 · 80810
Stability
Stable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
SKIN CONDITIONINGHAIR CONDITIONING
InChI
1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
InChIKey
ONIBWKKTOPOVIA-UHFFFAOYSA-N
SMILES
OC(=O)[C@@H]1CCCN1
LogP
-2.54 at · -2.54 at 20℃
CAS DataBase Reference
147 · 147-85-3(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
L-PROLINE
FDA 21 CFR
172.32 · 172.320
FDA UNII
9 DLQ4CIU6V · 9DLQ4CIU6V
NIST Chemistry Reference
Proline(147-85-3)
EPA Substance Registry System
L-Proline (147-85-3)
UNSPSC Code
41116107 · 41116107
NACRES
26 · NA.26
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P271-P280
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-22
Safety Statements
24 · 24/25-36/37/39-26
WGK Germany
3 · 3
RTECS
3584000 · TW3584000
F
3 · 3-10
TSCA
TSCA listed
HS Code
29339990 · 29339990
Storage Class
13 · 13 - Non Combustible Solids
Hazardous Substances Data
147 · 147-85-3(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: > 5110 mg/kg
REACH Registrations
Active

UsesL-Proline is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.

General DescriptionL-Proline is a non-essential amino acid, which is a building block of proteins. Peptides bond to proline, making it a useful building block for proteins. It can be used as a cell culture media component for the commercial biomanufacturing of therapeutic recombinant proteins and monoclonal antibodies. L-Proline plays important roles in various biological processes. It is involved in the synthesis of collagen, which is one of the most abundant proteins in the human body and provides structural support to tissues such as skin, bone, cartilage, and tendons.

Preparation methods · 1 item

PreparationSynthesis of L-proline: Using glutamic acid as a raw material, it is esterified with absolute ethanol under the catalysis of sulfuric acid, and triethanolamine is added to free the aminosulfate to obtain glutamic acid-δ-ethyl ester. The glutamic acid-δ-ethyl ester is then reduced with a metal reducing agent potassium borohydride to obtain crude proline, which is finally separated and purified to obtain crude L-proline.

Upstream & downstream products

Upstream raw materials

Picric acidD(+)-GlucoseL-Glutamic acidHydrolyzateTriethylamineIon exchange resin columnAmmonium chloridePotassium borohydrideChromatographyCaseinIsopropyl alcoholGelatinTriethanolamineAluminum oxide

Downstream products

D-(S)-3-acetylthio-2-methylpropionylL-prolineR(-)-denopamineEnalaprilD-Proline(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaboroleDL-ProlineLevosulpiride2-Fluoro-4-(methylsulfonyl)aniline(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanolLisinoprilCaptopril2-(2-Aminoethyl)-1-methylpyrrolidine(S)-2-MethylprolineMethyl L-prolinate hydrochloride(2S)-1-Methyl-2-Pyrrolidineethanol2-Pyrrolidinecarboxamide,1-(hydroxyacetyl)-,(S)-(9CI)Z-Pro-NH2
Additional notes · 1 item

DefinitionChEBI: L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion.