(R)-(-)-CITRAMALIC ACID

Base Information

• Chemical Name: (R)-(-)-CITRAMALIC ACID
• CAS No.: 6236-10-8
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• Mol file: 6236-10-8.mol

Synonyms:Butanedioicacid, 2-hydroxy-2-methyl-, (R)-;Malic acid, 2-methyl-, (-)- (8CI);(-)-Citramalic acid;(R)-Citramalate;(R)-Citramalic acid;2R-Methylmalic acid;D-(-)-Citramalic acid;D-Citramalic acid;R-Citramalic acid;

Chemical Property of (R)-(-)-CITRAMALIC ACID

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 0.000161mmHg at 25°C
• Melting Point: 108-110 °C(lit. )
• Refractive Index: 1.521
• Boiling Point: 295.2 °C at 760 mmHg
• PKA: 3.65±0.28(Predicted)
• Flash Point: 146.6 °C
• PSA: 94.83000
• Density: 1.513 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

D-(?)-Citramalic acid lithium salt ≥95.0% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-(-)-CITRAMALIC ACID

There total 19 articles about (R)-(-)-CITRAMALIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

((3R,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[2,1-c][1,4]oxazin-3-yl)-acetic acid ethyl ester (205579-47-1) → (R)-(-)-citramalic acid (6236-10-8,2306-22-1)

Guidance literature:

With hydrogenchloride; for 5h; Heating;

DOI:10.3987/COM-97-S(N)57

Reference yield: 91.0%

(S)-4-methyl-4-(trichloromethyl)-2-oxetanone (93206-60-1) → (R)-(-)-citramalic acid (6236-10-8,2306-22-1)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 18h;

DOI:10.1071/CH99091

Reference yield: 87.0%

trans-2-phenylcyclohexyl citramalate (119696-04-7) → (R)-(-)-citramalic acid (6236-10-8,2306-22-1)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 24h;

DOI:10.1021/jo00270a048

upstream raw materials:

2-hydroxy-2-methylbutane-1,4-dioic acid

(S)-4-methyl-4-(trichloromethyl)-2-oxetanone

trans-2-phenylcyclohexyl citramalate

citraconic acid

Downstream raw materials:

(R)-2-methyl-4-(phenylmethoxy)butane-1,2-diol

(R)-(+)-2,2,4-Trimethyl-4-<2-(benzyloxy)ethyl>-1,3-dioxolane

(R)-2-methyl-2-[2'-(phenylmethoxy)ethyl]oxirane

(S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal

Refernces

• 1、 Garcia Ruano, Jose L.,Fernandez-Ibaez,Martin Castro, Ana M.,Rodriguez Ramos, Jesus H.,Rubio Flamarique, Ana C.. "Regio- and stereocontrolled hydrocyanation of chiral 2-alkylglycidamides with Et2AlCN: Synthesis of enantiomerically pure mono- and disubstituted malic acid derivatives". . p. 1321 - 1325. Retrieved 2007/10/03.
• 2、 Gill, Melvyn,Harte, Michael F.,Ten, Abilio. "Pigments of Fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid". . p. 245 - 256. Retrieved 2007/10/03.