526-99-8

Basic information

• Product Name: MUCIC ACID
• Synonyms: SACCHAROLACTIC ACID;TETRAHYDROXYHEXANEDIOIC ACID;TETRAHYDROXYADIPIC ACID;MUCIC ACID;D-GALACTARIC ACID;GALACTOSACCHARIC ACID;GALACTARIC ACID;GALACTERIC ACID
• CAS NO: 526-99-8
• Molecular Formula: C₆H₁₀O₈
• Molecular Weight: 210.14
• EINECS: 208-404-0
• Product Categories: Plantago ovata;Building Blocks;C6;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Inhibitors
• Mol File: 526-99-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 220-225 °C (dec.)(lit.)
• Boiling Point: 269.65°C (rough estimate)
• Flash Point: 431.2oC
• Appearance: white to light beige fine crystalline powder
• Density: 1.5274 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 3.3g/l soluble
• PKA: 2.99±0.35(Predicted)
• Water Solubility: Soluble in water.
• Merck: 14,4331
• BRN: 1728117
• CAS DataBase Reference: MUCIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: MUCIC ACID(526-99-8)
• EPA Substance Registry System: MUCIC ACID(526-99-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-40
• Safety Statements: 22-24/25-36/37
• WGK Germany: 2
• RTECS: LW5180000
• TSCA: Yes
• Hazardous Substances Data: 526-99-8(Hazardous Substances Data)

Usage

Description

Mucic acid,C6H10O8 or HOOC-(CHOH)4-COOH, (also known as galactaric or meso - galactaric acid) is an aldaric acid obtained by nitric acid oxidation of galactose or galactose - containing compounds like lactose, dulcite, quercite, and most varieties of gum. It forms a crystalline powder, which melts at 230°C. It is insoluble in alcohol, and nearly insoluble in cold water. Due to the symmetry in the molecule, it is optically inactive even though it has chiral carbon atoms (i.e., it is a meso compound). When heated with pyridine to 140°C, it is converted into allommic acid. When digested with fuming hydrochloric acid for some time it is converted into a furfural dicarboxylic acid while on heating with barium sulfide it is transformed into athiophene carboxylic acid. The ammonium salt yields on dry distillation carbon dioxide, ammonia, pyrrol and other substances. The acid when fused with caustic alkalis yields oxalic acid. With potassium bisulfate mucic acid forms 3-hydroxy-2-pyrone by dehydration and decarboxylation.

Uses

Different sources of media describe the Uses of 526-99-8 differently. You can refer to the following data:
1. Mucic acid can be used to replace tartaric acid in self-rising flour or fizzies.
2. Mucic acid is used to replace tartaric acid in self-rising flour or fizzies. It is also used as a precursor of adipic acid en route to nylon by a rhenium-catalyzed deoxydehydration reaction. It replaces potassium bitartrate in baking powder and also used for manufacture of granular effervescing salts.
3. Substitute for tartaric acid, sequestrant for metalions (calcium, iron), retards hardening of concreteintermediate for synthesis of heterocyclic com-pounds (pyrroles).

Definition

ChEBI: A hexaric acid resulting from formal oxidative ring cleavage of galactose.

InChI:InChI=1/C6H10O8/c7-3(8)1-2-5(11,12)6(13,14)4(9)10/h11-14H,1-2H2,(H,7,8)(H,9,10)

Upstream product

• 608-66-2 D-galactitol 
• 3588-17-8 (2E,4E)-2,4-hexadienedioic acid 
• 117468-78-7 D-altraric acid 
• 527-00-4 allo-mucic acid 
• 117468-79-8 L-altraric acid 
• 512-69-6 D-raffinose 
• 113863-68-6 1,4-di-O-acetyl-5,6-O-isopropylidene-allo-inositol 
• 5469-75-0 (2R,3S,4R,5S)-2,3,4,5-tetraacetoxyhexanedioic acid 
• 2231-57-4 Thiocarbohydrazide 
• 88020-31-9 (2-Furyl)-(4-nitrobenzyl)-keton 
• 67-64-1 acetone 
• 7722-84-1 dihydrogen peroxide 
• 7697-37-2 nitric acid 
• 133-42-6 D-galactonic acid 

Downstream Products

• 15909-67-8 (2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-hexanedioic acid diethyl ester 
• 7404-38-8 idaric acid bis-(N'-phenyl-hydrazide) 
• 496-64-0 3-hydroxy-2-pyrone 
• 88-14-2 2-furanoic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 124-04-9 Adipic acid 
• 3238-40-2 furan-2,5-dicarboxylic acid 
• 133-37-9 DL-tartaric acid 
• 133-42-6 D-galactonic acid 
• 133-42-6 galactonic acid 
• 527-00-4 allo-mucic acid 
• 87-73-0 DL-altraric acid 
• 541-50-4 2-acetoacetic acid 
• 144-62-7 oxalic acid 

Relevant articles and documents

PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS

Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C5-C6 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C5-C6 aldonic acid and/or lactone(s) thereof and/or a C5-C6 aldose are described.

Biological Activities of Phenolics from the Fruits of Phyllanthus emblica L. (Euphorbiaceae)

Seven phenolic compounds, 1 – 7, including a new organic acid gallate, mucic acid 1-ethyl 6-methyl ester 2-O-gallate (7), were isolated from the MeOH extract of the fruits of Phyllanthus emblica L. (Euphorbiaceae). The structures were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluated for their antioxidant abilities by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) assays. The inhibitory activities against melanogenesis in B16 melanoma cells induced by α-MSH, as well as cytotoxic activities against four human cancer cell lines were also evaluated. All phenolic compounds, 1 – 7, exhibited potent antioxidant abilities (DPPH: IC50 5.6 – 12.9 μm; ABTS: 0.87 – 8.43 μm Trolox/μm; FRAP: 1.01 – 5.79 μm Fe2+/μm, respectively). Besides, 5 – 7, also exhibited moderate inhibitory activities against melanogenesis (80.7 – 86.8% melanin content), even with no or low toxicity to the cells (93.5 – 101.6% cell viability) at a high concentration of 100 μm. Compounds 1 – 3 exhibited cytotoxic activity against one or more cell lines (IC50 13.9 – 68.4%), and compound 1 with high tumor selectivity for A549 (SI 3.2).

Novel synthetic process of mucic acid

The present invention relates to a method of synthesizing mucic acid from galactose derived from biomass including marine resources, and more specifically, to a method of synthesizing mucic acid which utilizes galactose as a starting material and through a chemical reaction, induces an oxidation reaction to synthesize mucic acid. The method of the present invention can easily synthesize mucic acid in a high yield from galactose and the like under low temperature and atmospheric pressure operating conditions, can be used as an intermediate to produce bio adipic acid, the raw material of nylon 66 that is used as a material for automobile parts, and, therefore, has high industrial applicability.(AA) Marine bio sugar mixture obtained after saccharification using non-food marine resources (galactose, or a mixture of galactose, glucose and rhamnose)(BB) Mixing of aqueous nitric acid solution with sugar mixture(CC) Oxidation reaction of bio sugar under low temperature condition (-15~0anddeg;C)(DD) Washing of solid products produced from chemical reaction and extraction of high-purity mucic acid particles using aqueous solution, having mucic acid dissolved therein, prepared in advanceCOPYRIGHT KIPO 2017