454-28-4

Basic information

• Product Name: Homocysteine
• Synonyms: 2-Amino-4-mercaptobutanoic acid;Nsc43117
• CAS NO: 454-28-4
• Molecular Formula: C₄H₉NO₂S
• Molecular Weight: 0
• Mol File: 454-28-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Homocysteine(CAS DataBase Reference)
• NIST Chemistry Reference: Homocysteine(454-28-4)
• EPA Substance Registry System: Homocysteine(454-28-4)

Safety Data

• Hazardous Substances Data: 454-28-4(Hazardous Substances Data)

Usage

General Description

Homocysteine is a non-proteinogenic amino acid that is produced in the body as a byproduct of methionine metabolism. Elevated levels of homocysteine in the blood have been associated with an increased risk of cardiovascular disease, stroke, and other cardiovascular complications. This is thought to be due to the potential for homocysteine to promote inflammation, impair blood vessel function, and contribute to the development of atherosclerosis. Certain genetic factors, as well as deficiencies in B vitamins such as vitamin B6, vitamin B12, and folate, can lead to higher levels of homocysteine in the blood. Managing these deficiencies and reducing homocysteine levels through dietary and lifestyle changes may help to reduce the risk of associated cardiovascular conditions.

Upstream product

• 2867-15-4 (2S,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid 
• 454-29-5 2-amino-4-mercaptobutyric acid 
• 700-63-0 (R)-phenylglycine amide 
• 147331-82-6 (R)-1,3-thiazane-4-carboxylic acid 
• 6027-15-2 D-homocystine 
• 348-67-4 D-methionine 

Downstream Products

• 31982-10-2 meso-homolanthione 
• 6027-15-2 D-homocystine 
• 13073-47-7 S-benzyl-D-homocysteine 
• 130548-06-0 D-Homocysteine thiolactone 
• 6265-93-6 2-(2′-hydroxy-3′-methoxyphenyl)benzothiazole 
• 30651-43-5 (2R,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid 

Relevant articles and documents

Facile synthesis of optically active homocysteine from methionine

L-Methionine (L-Met) reacted with dichloroacetic acid in concentrated hydrochloric acid under refluxing to give (45)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [(4S)-TDC· HCl]. L-Homocysteine (L-Hcy) was obtained in an optically pure form by treatme

Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine

In order to synthesize four stereoisomers of cystathionine (CYT), D- and L-homocysteines (D- and L-Hcy) were synthesized from methionine (Met) by a facile procedure. L-Met was reacted with dichloroacetic acid in concentrated hydrochloric acid under reflux to give (4S)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [(4S)-TDC? HCl]. L-Hcy was obtained by treatment of (4S)-TDC? HCl with hydroxylamine. D-Hcy was also synthesized from D-Met via (4R)-TDC? HCl intermediate. The obtained D- and L-Hcy were condensed with (R)- and (S)-2-amino-3-chloropropanoic acid hydrochlorides under alkaline conditions to give four stereoisomers of CYT.

Preparations of Optically Active Homocysteine and Homocystine by Asymmetric Transformation of (RS)-1,3-Thiazane-4-carboxylic Acid

DL-Homocysteine from (RS)-homocysteine thiolactone hydrochloride was subjected to reaction with formaldehyde in acetic acid to give (RS)-1,3-thiazane-4-carboxylic acid monohydrate .An asymmetric transformation of (RS)-THA*H2O was achieved via salt formation with optically active tartaric acid in the presence of salicylaldehyde in acetic acid.The (R)- and (S)-THA obtained, respectively, from the salt of (R)-THA with (2R,3R)-tartaric acid and its enantiomeric salt were treated with hydroxylamine hydrochloride to give D- and L-Hcy of 100percent optical purity, respectively, in 50percent yield from (RS)-HTL*HCl.Oxidation of D- and L-Hcy with hydrogen peroxide gave D- and L-homocystine, respectively, in 47percent yield.