(2S)-2-amino-3-hydroxypropanoic acid

• ChemBase ID: 19
• Molecular Formular: C3H7NO3
• Molecular Mass: 105.09258
• Monoisotopic Mass: 105.04259309
• SMILES: OC[C@H](N)C(=O)O
• Canonical SMILES: OC[C@@H](C(=O)O)N
• InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
• InChIKey: MTCFGRXMJLQNBG-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-hydroxypropanoic acid
• IUPAC Traditional name: L-serine
• Synonyms: H-Ser-OH; L-2-Amino-3-hydroxypropionic acid; (S)-2-Amino-3-hydroxypropanoic acid; Hydroxyalanine; 2-Amino-3-hydroxypropanoic acid; Serine; (-)-Serine; Serine; L-Ser; L-3-Hydroxy-2-aminopropionic acid; L-(-)-Serine; b-Hydroxy-L-alanine; 3-Hydroxyalanine; 2-Amino-3-hydroxypropionic acid; (S)-Serine; (S)-a-Amino-b-hydroxypropionic acid; (S)-2-Amino-3-hydroxypropanoic acid; L-Serine; beta-HYDROXYALANINE; L-SERINE, USP GRADE; L-Serine; (S)-2-Amino-3-hydroxypropionic acid; Serinum; (S)-2-氨基-3-羟基丙酸; L-丝氨酸; 丝氨酸

Database IDs

• CAS Number: 56-45-1
• EC Number: 206-130-6; 200-274-3
• MDL Number: MFCD00064224
• Beilstein Number: 1721404
• Merck Index: 148460
• PubChem SID: 24899473; 24899605; 24888286; 46506450; 160963482; 24899599; 24887156
• PubChem CID: 5951; 617
• CHEBI ID: 17115
• CHEMBL: 11298
• Chemspider ID: 5736
• DrugBank ID: DB00133
• IUPHAR ligand ID: 726
• Unique Ingredient Identifier: 452VLY9402
• Wikipedia Title: Serine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.03399
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.8875728
• LogD (pH = 7.4): -3.8992038
• Log P: -3.8877351
• Molar Refractivity: 22.041 cm^3
• Polarizability: 9.0643015 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.42
• LOG S: 0.66
• Solubility (Water): 4.80e+02 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble0.5 M at 20 °C, clear, colorless; 425 g/L; H2O: soluble50 mg/mL; soluble in water
• Apperance: powder; white crystals or powder
• Melting Point: > 228°C; 214-224°C dec.; 222 °C (dec.)(lit.); 246 °C decomp.
• Density: 1.603 g/cm^3 (22 °C)
• Optical Rotation: [α]20/D +13±0.5°, c = 5% in 5 M HCl; [α]20/D +13±1°, c = 5% in 5 M HCl; +15 (c=9 in 1N HCl)
• Absorption Wavelength: λ: 260 nm Amax: 0.05; λ: 280 nm Amax: 0.05
• Hydrophobicity(logP): -4
• pKa: 2.21 (carboxyl), 9.15 (amino)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: VT8100000
• German water hazard class: 1
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥98.5%; ≥99% (TLC); ≥99.0% (NT); ≥99.5% (NT); 95+%; 97%; 98%; 98.5-101.0%; 99%
• Grade: certified reference material; EP; Ph Eur; PharmaGrade; ReagentPlus®; TraceCERT®; USP
• Suitability: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.3% foreign amino acids; ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤50 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from non-animal source
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV); ≤0.2% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• λ: 0.5 M in 1 M HCl
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra
• Linear Formula: HOCH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02199560

White powder

MP Biomedicals - 02194737

Cell Culture Reagent
Purity: 99+%
Crystalline

MP Biomedicals - 02102873

Purity: 99+%
Crystalline

DrugBank - DB03375

Drug information: experimental

DrugBank - DB00133

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from glycine or threonine. It is involved in the biosynthesis of purines; pyrimidines; and other amino acids. [PubChem]
• Indication: Used as a natural moisturizing agent in some cosmetics and skin care products.
• Pharmacology: Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - S4311

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。

Sigma Aldrich - S1315

Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - S4500

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
包装
1 kg in poly bottle
1, 100 g in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 84959

Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
Other Notes
Synthesis of labels for protonation studies by Fourier Transform infrared methods1; Stabilizes mung bean nuclease at pH values below seven2; Amino acid spacing in isotachophoresis on polyacrylamide gel - a critical evaluation3; Growth requirement of various microorganisms4

Sigma Aldrich - 78682

Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.

Sigma Aldrich - 54763

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.
Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
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 - 84960

Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.

REFERENCES

• Has been used in a synthesis of D-amino acids. The configuration is inverted by conversion of the carboxyl group to the new alkyl chain by reaction with an organolithium reagent to give the ketone, which is deoxygenated by Raney nickel desulfurization of the thioketal, the hydroxymethyl group becoming the new carboxyl group by oxidation with oxygen over a Pt catalyst: J. Am. Chem. Soc., 106, 1095 (1984):