Malic acid - CAS 6915-15-7

Catalog:	BB033710
Product Name:	Malic acid
CAS:	6915-15-7
Synonyms:	Hydroxybutanedioic acid; (RS)-(±)-Hydroxybutanedioic acid; Malic acid; (±)-2-Hydroxysuccinic acid; DL-Hydroxybutanedioic acid
Application:	The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.

Technical Data

Related CAS:	617-48-1
IUPAC Name:	2-hydroxybutanedioic acid
Description:	Malic acid supplementation may be useful for conservative treatment of calcium renal stone disease by virtue of its capacity to induce these effects.
Molecular Weight:	134.09
Molecular Formula:	C4H6O5
Canonical SMILES:	C(C(C(=O)O)O)C(=O)O
InChI:	InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
InChI Key:	BJEPYKJPYRNKOW-UHFFFAOYSA-N
Boiling Point:	306.4 ℃ at 760 mmHg
Melting Point:	131-133°C
Purity:	>98%
Density:	1.641 g/cm³
Solubility:	Soluble in Methanol
Appearance:	White or Nearly White Crystalline Powder
Storage:	Store at 2-8°C
Decomposition:	When heated to decomposition it emits acrid smoke and irritating fumes
LogP:	-1.09340
Quality Standard:	Enterprise Standard
pH:	pH of a 0.001% aqueous solution is 3.80, that of 0.1% solution is 2.80, and that of a 1.0% solution is 2.34
Stability:	Stable under recommended storage conditions
Vapor Pressure:	0.00000293 [mmHg]

GHS Hazard Statement:	H315 (79.02%): Causes skin irritation [Warning Skin corrosion/irritation]
Precautionary Statement:	P264, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P337+P313, and P362
Signal Word:	Danger

Publication Number	Title	Priority Date
US-2015065482-A1	Alkynyl alcohols and methods of use	20130822
US-2016096850-A9	Alkynyl alcohols and methods of use	20130822
US-2016200739-A1	Alkynyl alcohols and methods of use	20130822
US-2016031787-A1	Synthesis of biobased and substituted terephthalic acids and isophthalic acids	20130315
US-2014179778-A1	Cocrystals of (n,n-diethylcarbamoyl)methyl methyl (2e)but-2-ene-1,4-dioate	20121105

PMID	Publication Date	Title	Journal
29968805	20180703	Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics	Scientific reports
29128607	20180105	Effects of a new antiprotozoal drug, N,N'-diphenyl-4-methoxy-benzamidine, on energy-linked functions of rat liver mitochondria	Chemico-biological interactions
28223344	20170301	An Intestinal Farnesoid X Receptor-Ceramide Signaling Axis Modulates Hepatic Gluconeogenesis in Mice	Diabetes
28108222	20170225	Diquat-induced cellular pyridine nucleotide redox changes and alteration of metabolic enzyme activities in colonic carcinoma cells	Chemico-biological interactions
27469509	20161101	A small molecule inhibitor of mutant IDH2 rescues cardiomyopathy in a D-2-hydroxyglutaric aciduria type II mouse model	Journal of inherited metabolic disease

Complexity:	129
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Exact Mass:	134.02152329
Formal Charge:	0
Heavy Atom Count:	9
Hydrogen Bond Acceptor Count:	5
Hydrogen Bond Donor Count:	3
Isotope Atom Count:	0
Monoisotopic Mass:	134.02152329
Rotatable Bond Count:	3
Topological Polar Surface Area:	94.8 Å²
Undefined Atom Stereocenter Count:	1
Undefined Bond Stereocenter Count:	0
XLogP3:	-1.3