L-Serine
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L-Serine
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CAS No:
56-45-1
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Formula:
C3H7NO3
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Chemical Name:
L-Serine
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Synonyms:
L-Serine;Serine,L-;(S)-α-Amino-β-hydroxypropionic acid;β-Hydroxy-L-alanine;Serine;L-(-)-Serine;Propanoic acid,2-amino-3-hydroxy-,(S)-;(S)-2-Amino-3-hydroxypropanoic acid;(S)-Serine;L-3-Hydroxy-2-aminopropionic acid;(-)-Serine;L-Alanine,3-hydroxy-;L-Ser;(2S)-2-Amino-3-hydroxypropanoic acid;(2S)-2-Azaniumyl-3-hydroxypropanoate;2: PN: WO2020113403 TABLE: L1 claimed sequence;4: PN: WO2020191289 PAGE: 118 claimed sequence;10: PN: WO2021055880 SEQID: 11 claimed protein;6898-95-9;154605-73-9
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CAS No:
Description
L-Serine, one of the so-called non-essential amino acids, plays a central role in cellular proliferation.
Solid
L-serine is the L-enantiomer of serine. It has a role as a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a serine family amino acid, a proteinogenic amino acid, a L-alpha-amino acid and a serine. It is a conjugate base of a L-serinium. It is a conjugate acid of a L-serinate. It is an enantiomer of a D-serine. It is a tautomer of a L-serine zwitterion.|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.|Serine is a non-essential amino acid in humans (synthesized by the body), Serine is present and functionally important in many proteins. With an alcohol group, serine is needed for the metabolism of fats, fatty acids, and cell membranes; muscle growth; and a healthy immune system. It also plays a major role in pyrimidine, purine, creatine, and porphyrin biosynthetic pathways. Serine is also found at the active site of the serine protease enzyme class that includes trypsin and chymotrypsin. (NCI04)|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.
L-Serine Basic Attributes
105.09300
105.09
200-274-3
452VLY9402
760115
C29613
HEXAGONAL PLATES OR PRISMS|COLORLESS CRYSTALS
29225000
Characteristics
83.55000
-3.1
Solid
1.6 g/cm3 @ Temp: 22 °C
228 °C (decomp)
394.8ºC at 760mmHg
192.6ºC
1.519
H2O: 425.0 mg/mL;425.0 mg/mL
Store at 0-5ºC
SPECIFIC OPTICAL ROTATION: -6.83 DEG @ 20 °C/D (1.5 G IN 15 G AQ SOLN); +14.45 DEG @ 25 °C/D (C= 0.5 G IN 5.6 NORMAL HCL)
SWEETISH TASTE, INSIPID AFTERTASTE
2.21(at 25 °C)
2.21 (at 25 °C)|pKa = 2.21; pKb = 9.15
136.66 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|136.2 Ų [M-H]-
DECOMPOSES @ 228 °C; SUBLIMES @ 150 °C IN HIGH VACUUM (10-4 MM HG); MOLECULAR ROTATION IN 5 N HCL +15.0 DEG|OPTICALLY ACTIVE
Safety Information
NONH for all modes of transport
3
R36/37/38
S24/25
VT8100000
Xi
Stable. Incompatible with strong oxidizing agents.
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
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.
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).
Not Classified
Toxicity
INTRACEREBROVENTRICULAR INJECTIONS OF ALANINE (0.5-2.0 UG) INTO RABBITS CAUSED DECR IN BODY TEMP IN A 10-DEG ENVIRONMENT. THE EFFECT WAS SLIGHTLY SUBADDITIVE WITH THAT OF SERINE.|ERYTHROBLASTIC LEUKEMIC CELLS INCUBATED IN MEDIA CONTAINING ESSENTIAL AMINO ACID L-SERINE BOUND APPROX 30% MORE INSULIN LABELED WITH (125)IODINE THAN THOSE INCUBATED WITHOUT SERINE.
NATURALLY OCCURRING FORM IS L-SERINE.
Drug Information
Used as a natural moisturizing agent in some cosmetics and skin care products.|Parenteral nutrition|Supplementation of amino-acids where parenteral nutrition is required.
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.
IN PT AGE 2-9 YR, SERINE PRESENT IN ACID MUCOPOLYSACCHARIDES. EXCESSIVE ACCUMULATION & EXCRETION IN URINE OF MUCOPOLYSACCHARIDES MAY BE RELATED TO ABNORMAL BONDING BETWEEN MUCOPOLYSACCHARIDES & PROTEIN.|IN PT AGE 2-9 YR, URINARY SERINE EXCRETION INCR FROM 0.059-0.162 UMOL/24 HR & PLASMA SERINE LEVELS INCR FROM 0.102-0.158 UMOL/ML.|IN PT AGE 2-9 YR, SERINE IS PROBABLY NOT ESTERIFIED THROUGH ITS BETA-HYDROXYL GROUP TO ACID MUCOPOLYSACCHARIDES BUT IS LINKED BY CARBOXYL GROUP.|DETERMINATION OF SERINE LEVELS IN 13 REGIONS OF THE RAT CEREBRAL CORTEX FAILED TO SHOW ANY MARKED DIFFERENCES IN THE AMINO ACID CONTENTS OF CORTEX AREAS OF DIVERSE FUNCTIONS.
L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.
HUMAN NEUROBLASTOMA SK-N-SH-SY5Y (5Y) CELLS WERE CULTURED WITH SUPPLEMENTAL SERINE FOR 3-6 DAYS. SERINE HYDROXYMETHYLTRANSFERASE WAS ASSAYED. NO CHANGES IN SPECIFIC ACTIVITY OR CELLULAR MORPHOLOGY WERE NOTED @ CONCN LESS THAN 16 UMOL.|METABOLIC EFFECTS OF CONTROLLED MODIFIED INTAKES OF L-SERINE IN PARENTERAL NUTRITION SOLUTIONS WERE INVESTIGATED IN NORMAL ADULTS.
L Serine
L-Serine Use and Manufacturing
ISOLATED FROM SILK FIBROIN (SERICINE)|Production methods for L-serine include extraction and fermentation; extraction of hydrolysates and fermentation of glycine substrate are the preferred methods for producing L-serine... microorganisms suggested for the fermentation production of L-serine from glycine include mutants of the genera Pseudomonas, Corynebacterium glycinophilum, and Norcardia|Hydrolysis of protein (especially silk protein); synthesized from glycine
Medical use: parenteral nutrition, dietary supplement.Used as biochemical reagents and food additives.It is used in biochemical research, preparation of tissue culture medium, and amino acid nutrition medicine in medicine.
World market for L-serine in 1982: 50 tonnes
Flavor, food and pharmaceutical grades; USP and FCC grades
L-Serine: ACTIVE|AMINO ACID COMPOSITION OF SELECTED PROTEINS. SERINE: GELATINS 3.8 G/100 G PROTEIN; MIXED PROTEINS 4.3 G/LB G TOTAL NITROGEN; CASEIN 6.3 G/100 G PROTEIN; SERUM ALBUMIN 7.0 G/100 G PROTEIN; GAMMA-GLOBULIN 11.4 G/100 G PROTEIN; HEMOGLOBIN: HORSE 5.8 G/100 G PROTEIN; INSULIN 5.2 G/100 G PROTEIN; CLOSTRIDIUM BOTULINUM TOXIN 4.4 G/100 G PROTEIN /FROM TABLE/|L- AND D-SERINE EXHIBIT SIMILAR SWEET TASTE QUALITIES.|L-serine can be chemically produced by reacting glycine with formaldehyde
TESTS FOR...AMINO ACIDS...CHROMATOGRAPHIC, ELECTROPHORETIC... HYDROLYSIS OF PROTEIN YIELDS AMINO ACIDS... /PRC: USE AMINO ACID ANALYZER TO DETERMINE/|AOAC method 960.47, Amino Acids in Vitamin Preparations; microbiological method using basal media|The following methods have been developed for the analysis of free amino acids in blood, food, and feedstocks: (1) Protein hydrolysis, (2) Chromatographic methods that include high performance liquid chromatography (HPLC), gas chromatography (GC) and thin-layer chromatography (TLC), (3) Colorimetric and Fluorimetric Analysis, (4) Spectrometric Analysis, and (5) Enzymatic Determination and Microbial Assay
Human Drugs -> EU pediatric investigation plans|Cosmetics -> Antistatic; Hair conditioning; Skin conditioning
Computed Properties
Molecular Weight:105.09
XLogP3:-3.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:105.042593085
Monoisotopic Mass:105.042593085
Topological Polar Surface Area:83.6
Heavy Atom Count:7
Complexity:72.6
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Amino acids are the basic units that make up human proteins and enzymes. They are the raw materials for synthesizing hormones, participate in human metabolism and various physiological functions, and play a special role in life.
Registered Holders
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AJINOMOTO HEALTH AND NUTRITION NORTH AMERICA INC
Active
United States
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Evonik Rexim S.A.S.
Active
Japan
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Evonik Rexim (Nanning) Pharmaceutical Co.,Ltd.
Active
Japan
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