D-Proline
- Iupac Name：(2R)-pyrrolidine-2-carboxylic acid
- CAS No.: 344-25-2
- Molecular Weight：115.13046
- Modify Date.: 2022-11-01 09:55
- Introduction:
D-Proline, with the chemical formula C5H9NO2 and CAS registry number 344-25-2, is a non-essential amino acid that is naturally occurring in the human body. It is an isomer of L-Proline and is commonly found in proteins and peptides. D-Proline plays a crucial role in the synthesis of collagen, which is essential for the structure and function of connective tissues, skin, and bones. It is also involved in the production of neurotransmitters and the regulation of immune responses. D-Proline is used in the pharmaceutical industry for the synthesis of various drugs, including antiviral and anticancer agents. Additionally, it has applications in the field of organic chemistry as a chiral building block for the synthesis of complex molecules. Overall, D-Proline is a vital compound with diverse biological and chemical significance.
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1. Names and Identifiers
- 1.1 Name
- D-Proline
- 1.2 Synonyms
(+)-(R)-Proline (2R)-Pyrrolidin-1-ium-2-carboxylate (2R)-Pyrrolidine-2-carboxylic acid (R)-(+)-PROLINE (R)-2-Carboxypyrrolidine (R)-Proline (R)-PYRROLIDINE-2-CARBOXYLIC ACID D-(+)-Proline D(+)-PROLINE D-2-PYRROLIDINECARBOXYLIC ACID D-Pro-OH D-PYRROLIDINE-2-CARBOXYLIC ACID H-D-Pro-OH Proline, D-
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- 1.3 CAS No.
- 344-25-2
- 1.4 CID
- 8988
- 1.5 EINECS(EC#)
- 206-452-7
- 1.6 Molecular Formula
- C5H9NO2 (isomer)
- 1.7 Inchi
- InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
- 1.8 InChIkey
- ONIBWKKTOPOVIA-SCSAIBSYSA-N
- 1.9 Canonical Smiles
- C1CC(NC1)C(=O)O
- 1.10 Isomers Smiles
- C1C[C@@H](NC1)C(=O)O
2. Properties
- 2.1 Density
- 1.186
- 2.1 Melting point
- 223℃
- 2.1 Boiling point
- 252.2 °C at 760 mmHg
- 2.1 Refractive index
- 85 ° (C=4, H2O)
- 2.1 Flash Point
- 106.3 °C
- 2.1 Precise Quality
- 115.06300
- 2.1 PSA
- 49.33000
- 2.1 logP
- 0.15180
- 2.1 Solubility
- soluble >1000 g/L (20 ºC)
- 2.2 Appearance
- White to off-white powder
- 2.3 Storage
- Hygroscopic. Store under Nitrogen. Ambient temperatures.
- 2.4 Chemical Properties
- White to off-white powder
- 2.5 Color/Form
- White to Yellow Solid
- 2.6 Decomposition
- When heated to decomposition it emits toxic vapors of /nitrogen oxides/.
- 2.7 Odor
- Odorless
- 2.8 pKa
- 1.952(at 25℃)
- 2.9 Water Solubility
- Soluble
- 2.10 Spectral Properties
- SPECIFIC OPTICAL ROTATION: -80.9 DEG @ 20 DEG C/D (WATER, 1%); SADTLER REF NUMBER: 1905 (IR, PRISM)
SPECIFIC OPTICAL ROTATION: -85.0 @ 23.4 DEG C/D (WATER, 1%); -52.6 @ 20 DEG C/D (0.50 N HYDROCHLORIC ACID, 0.58%); -93.9 DEG @ 20 DEG C/D (0.6 N POTASSIUM HYDROXIDE, 2.4%)
IR: 21030 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-52 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 7565 (Sadtler Research Laboratories Spectral Collection)
MASS: 4037 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
- 2.11 Stability
- Stable under normal temperatures and pressures.
- 2.12 StorageTemp
- Store at RT.
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: The D-enantiomer of proline.
- 3.2 Usage
- Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi; Xn
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
- 4.2 Octanol/Water Partition Coefficient
- Log P = -2.54
- 4.3 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.4 RIDADR
- 25kgs
- 4.4 Formulations/Preparations
- USP and FCC grades
- 4.5 WGK Germany
- 3
- 4.5 Safety
-
Hazard Codes of D-Proline (CAS NO.344-25-2):?
Xi,
Xn
Risk Statements: 22-36/37/38?
R22: Harmful if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36/37/39-26?
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
F: 3-10
Hazard Note: Irritant
- 4.6 Specification
-
?D-Proline , with CAS number of 344-25-2, can be called (2R)-2-Pyrrolidinecarboxylic acid ; (R)-(+)-Proline ; (+)-(R)-Proline ; (R)-Proline ; (R)-Pyrrolidine-2-carboxylic acid?;?D-(+)-Proline; D-Pyrrolidine-2-carboxylic acid ;?(R)-pyrrolidine-2-carboxylic acid .?It is a?white to off-white powder.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
344-25-2Total: 21 Synthesis Route
9. Other Information
- 9.0 Usage
- D-Proline is an essential component of collagen and is important for proper functioning of joints and tendons. It is also used as asymmetric catalysts in proline organocatalysis reactions.
10. Computational chemical data
- Molecular Weight: 115.13046g/mol
- Molecular Formula: C5H9NO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 115.063328530
- Monoisotopic Mass: 115.063328530
- Complexity: 103
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 49.3
- Heavy Atom Count: 8
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBiMAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACCjBgAQACALAAgAIAACQCAAAAAAAAAAAAIGIAAACABIAgCAEQAAEEACQAACYEQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
General Description D-Proline, a non-canonical amino acid with a unique distribution pattern in biological systems, plays a crucial role in pharmaceutical synthesis. Its presence in specific proteins ..
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General Description D-Proline accumulation in plants is a common response to various environmental stresses. It serves adaptive functions by acting as a compatible osmolyte, scavenging reactive oxygen..
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D-proline (D-Pro), also known as D-hydroxypyrrole carboxylic acid, is a crucial five-membered cyclic amino acid and chiral compound. It serves as both a splitting agent and a chiral reagent, as well a..
-
D-Proline, also known as D-Proline, is a white or light yellow solid powder at room temperature and pressure. It belongs to the class of amino acid derivatives and is widely used as an organic synthes..
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13. Realated Product Infomation
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