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Home> Encyclopedia >Pharmaceutical Intermediates>Vitamins, Amino Acids and Coenzymes>Organic Intermediate
D-Serine structure
D-Serine structure

D-Serine

Iupac Name:(2R)-2-amino-3-hydroxypropanoic acid
CAS No.: 312-84-5
Molecular Weight:105.093
Modify Date.: 2022-11-29 10:23
Introduction: A proteinogenic amino acids involved in the biosynthesis of purines and pyrimidines. Inhibitor of serine palmitoyltransferase. A neuromodulator. View more+
1. Names and Identifiers
1.1 Name
D-Serine
1.2 Synonyms

(2R)-2-amino-3-hydroxypropanoic acid (R)-2-amino-3-hydroxypropanoic acid (R)-Serine D-(+)-Serine D-2-Amino-3-hydroxypropanoic acid D-Serin H-D-Ser-OH NSC 77689 Serine D-form Serine, D-

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1.3 CAS No.
312-84-5
1.4 CID
71077
1.5 EINECS(EC#)
206-229-4
1.6 Molecular Formula
C3H7NO3 (isomer)
1.7 Inchi
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
1.8 InChIkey
MTCFGRXMJLQNBG-UWTATZPHSA-N
1.9 Canonical Smiles
C(C(C(=O)O)N)O
1.10 Isomers Smiles
C([C@H](C(=O)O)N)O
2. Properties
2.1 Density
1.415
2.1 Melting point
220℃
2.1 Boiling point
394.8°Cat760mmHg
2.1 Refractive index
1.4368 (estimate)
2.1 Flash Point
192.6°C
2.1 Precise Quality
105.04300
2.1 PSA
83.55000
2.1 logP
-0.90910
2.1 Solubility
H2O: 0.1?g/mL, clear, colorless
2.2 Appearance
Solid
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
White powder
2.5 Color/Form
HEXAGONAL PLATES OR PRISMS
COLORLESS CRYSTALS
2.6 Physical
Solid
2.7 pKa
2.16±0.10(Predicted)
2.8 Water Solubility
H2O: 346 g/L (20 oC)
2.9 Spectral Properties
SPECIFIC OPTICAL ROTATION: -6.83 DEG @ 20 DEG C/D (1.5 G IN 15 G AQ SOLN); +14.45 DEG @ 25 DEG C/D (C= 0.5 G IN 5.6 NORMAL HCL)
IR: 1593 (Sadtler Research Laboratories IR Grating Collection)
NMR: 9189 (Sadtler Research Laboratories Spectral Collection)
MASS: 4017 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
2.10 Stability
Stable under normal temperatures and pressures.
2.11 StorageTemp
Store at RT.
3. Use and Manufacturing
3.1 Definition
ChEBI: The R-enantiomer of serine. D-Serine Preparation Products And Raw materials Raw materials
3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 13 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 11 of 13 companies. For more detailed information, please visit ECHA C&L website

Of the 2 notification(s) provided by 2 of 13 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
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3.3 Usage
A proteinogenic amino acids involved in the biosynthesis of purines and pyrimidines. Inhibitor of serine palmitoyltransferase. A neuromodulator.
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/37/38
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
LogP = -3.07
4.3 Hazard Declaration
H315
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
NONH for all modes of transport
4.4 Caution Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
4.4 Formulations/Preparations
Flavor, food and pharmaceutical grades; USP and FCC grades
4.5 WGK Germany
3
4.5 RTECS
VT8200000
4.5 Specification

The D-Serine, with the cas register number 312-84-5, has other names as d-(+)-serine; d-serine; d-2-amino-3-hydroxypropionic acid; d-2-amino-3-hydroxypropanoic acid; d-beta-hydroxyalanine; h-d-ser-oh; 2-amino-3-hydroxypropanoic acid; (r)-2-amino-3-hydroxypropionic acid.

The physical characteristics of this chemical could be summarized as: (1)ACD/LogP: -1.58; (2)ACD/LogD (pH 5.5): -4.08; (3)ACD/LogD (pH 7.4): -4.08; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 38.77; (12)Index of Refraction: 1.519; (13)Molar Refractivity: 22.54 cm3; (14)Molar Volume: 74.2 cm3; (15)Polarizability: 8.93 ×10-24 cm3; (16)Surface Tension: 72.2 dyne/cm; (17)Density: 1.415 g/cm3; (18)Flash Point: 192.6 °C; (19)Enthalpy of Vaporization: 74.56 kJ/mol; (20)Boiling Point: 394.8 °C at 760 mmHg; (21)Vapour Pressure: 7.17E-08 mmHg at 25°C.

This is a kind of white powder, and its water solubility is 346 g/L (20 oC). Being among the irritant chemicals, it is irritating to eyes, respiratory system and skin, and it may cause inflammation to the skin or other mucous membranes. So while dealing with this chemical, you should be very cautious and had better take the following instructions. The first important thing is to wear suitable protective clothing. And avoid contact with skin and eyes, if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. And you could also convert to the WGK Germany? 3 to get more safety information.

When comes to its usage, it is widely applied in many ways. It could be used in curing inflammatory disease, such as temple arteritis and multiple rheumatic disease; Then it could also be used in biochemical study, preparation in TCM Tissue Culture Medium, Amino Acids-like nutriceutical in medicine; Besides, it could also be as the pharmaceutic intermediate and chemical reagents.
?
As to its product categories, there are various, including amino acid derivatives; serine [ser, s]; amino acids and derivatives; alpha-amino acids; amino acids; biochemistry; amino acids; glutamate receptor; glutamate; while its raw materials are chloroacetyl chloride, 2-n-butoxyethyl methacrylate, dl-serine, and aminoacylase.

The simple way to produce this chemical is below: DL-serine reacts with chloroacetic chloride in alkaling conndition and then go through a list of process of decompressing, drying by distillation, extracting by ethyl acetate, and then have the activated carbontreatment and splitting of acylaseI, finally, you could get this chemical.

In addition, you could refer to the following information to obtain the molecular structure:
SMILES:O=C(O)[C@H](N)CO
InChI:InChI=1/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
InChIKey:MTCFGRXMJLQNBG-UWTATZPHBH

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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

8. Other Information
8.0 Usage
D-Serine is involved in the biosynthesis of purines, pyrimidines, and other amino acids. D-Serine also is an agonist of glycine site of the NMDA-type glutamate receptor. It also acts as Lacosamide intermediate.
8.1 Manufacturing Info
D-Serine: ACTIVE
9. Computational chemical data
  • Molecular Weight: 105.093g/mol
  • Molecular Formula: C3H7NO3
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 105.042593085
  • Monoisotopic Mass: 105.042593085
  • Complexity: 72.6
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 83.6
  • Heavy Atom Count: 7
  • 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: AAADcYBCMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACCjhgAYACABAAgAIAACQCAAAAAAAAAAAAIGAAAACEAQAAAAAQAABMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
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12. Realated Product Infomation