454-29-5

Basic information

• Product Name: DL-Homocysteine
• Synonyms: DL-Homocysteine,95%;HOMOCYSTEINE, DL-(P);DL-Homocysteine,2-Amino-4-mercaptobutyric acid;DL-HoMocystein;(+-)-homocysteine;dl-2-amino-4-mercaptobutyricacid;usafb-12;2-AMINO-4-MERCAPTOBUTYRIC ACID
• CAS NO: 454-29-5
• Molecular Formula: C₄H₉NO₂S
• Molecular Weight: 135.18
• EINECS: 207-222-9
• Product Categories: Amino Acids;Amino Acids
• Mol File: 454-29-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 232-233 °C(lit.)
• Boiling Point: 299.691 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /solid
• Density: 1.149 (estimate)
• Vapor Pressure: 0.000278mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• PKA: 2.22, 8.87, 10.86(at 25℃)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,4734
• BRN: 1721683
• CAS DataBase Reference: DL-Homocysteine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Homocysteine(454-29-5)
• EPA Substance Registry System: DL-Homocysteine(454-29-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: MT0175000
• F: 10-23
• Hazardous Substances Data: 454-29-5(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

DL-Homocysteine has been used to induce hyperhomocysteinemia in Sprague–Dawley rats. It has also been used to study the effects of hyperhomocysteinemia on atherosclerosis in apolipoprotein E-deficient mice.

Definition

ChEBI: A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.

Biochem/physiol Actions

Homocysteine is a sulfhydryl-containing amino acid, synthesized from methionine. It is a non-essential, non-proteinogenic amino acid. It is an important determinant of the methylation cycle and is present in the plasma in four forms. An abnormally high level of homocysteine leads to hyperhomocysteinemia and also promotes atherosclerosis.

Purification Methods

Purify it as for the L-isomer. [Allen & Steinmann J Am Chem Soc 74 3932 1952, and references for the L-isomer above, Beilstein 4 IV 3189.]

InChI:InChI=1/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m1/s1

Upstream product

• 59-51-8 DL-methionine 
• 462-10-2 DL-homocystine 
• 6027-15-2 D-homocystine 
• 147331-82-6 (R)-1,3-thiazane-4-carboxylic acid 
• 700-63-0 (R)-phenylglycine amide 
• 348-67-4 D-methionine 
• 2867-15-4 (2S,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid 
• 10593-85-8 DL-homocysteine thiolactone 
• 1192-20-7 2-aminobutyrolactone 
• 187878-81-5 S-nitroso-homocysteine 
• 6038-19-3 3-aminodihydrothiophen-2(3H)-one hydrochloride 
• 1017-76-1 S-benzyl homocysteine 

Downstream Products

• 60175-95-3 1,3-thiazane-4-carboxylic acid 
• 56-88-2 DL,DL-cystathionine 
• 59-51-8 DL-methionine 
• 462-10-2 DL-homocystine 
• 100795-85-5 N-benzoyl-S-cyanomethyl-homocysteine 
• 5461-80-3 3-amino-2,5,6,7-tetrahydro-[1,4]thiazepine-5-carboxylic acid 
• 53276-26-9 (S)-5’-(S)-(3-amino-3-carboxypropyl)-5’-thioadenosine 
• 979-92-0 S-(5'-adenosyl)-L-homocysteine 
• 17055-00-4 6-(S-DL-Homocysteinyl)-4-methyl-brenzcatechin 
• 99855-86-4 S-benzoyl-DL-homocysteine 
• 348-67-4 D-methionine 
• 63-68-3 L-methionine 
• 31982-10-2 meso-homolanthione 
• 6027-15-2 D-homocystine 

Relevant articles and documents

New thiazane and thiazolidine PNA monomers: Synthesis, incorporation into PNAs and hybridization studies

New constrained PNA monomers containing a substituted thiazolidine or a thiazane ring were synthesized and incorporated in the center of a 9-mer homothymine PNA. The PNA/DNA hybrids stability was studied by UV-melting experiments which showed that the presence of the modified unit destabilizes the PNA/DNA triplexes.

An Organodiselenide with Dual Mimic Function of Sulfhydryl Oxidases and Glutathione Peroxidases: Aerial Oxidation of Organothiols to Organodisulfides

A novel organodiselenide, which mimics sulfhydryl oxidases and glutathione peroxidase (GPx) enzymes for oxidation of thiols by oxygen and hydrogen peroxide, respectively, into disulfides has been presented. The developed catalyst oxidizes an array of organothiols into respective disulfides in practical yields by using aerial O2 to avoid any reagents/additives, base, and light source. The synthesized diselenide also catalyzes the reduction of hydrogen peroxide into water by following the GPx enzymatic catalytic cycle with a reduction rate of 49.65 ± 3.7 μM·min-1.

Reaction of hydrogen sulfide with disulfide and Sulfenic acid to form the strongly Nucleophilic Persulfide

Background: Hydrogen sulfide (H2S) modulates physiological processes in mammals. Results: The reactivity of H2S toward disulfides (RSSR) and albumin sulfenic acid (RSOH) to form persulfides (RSSH) was assessed. Conclusion: H2S is less reactive than thiols. Persulfides have enhanced nucleophilicity. Significance: This kinetic study helps rationalize the contribution of the reactions with oxidized thiol derivatives toH2S biology.