PRODUCTS

GALACTARIC ACID

Galactaric acid is a hexaric acid resulting from formal oxidative ring cleavage of galactose.
Galactaric acid has a role as a human metabolite.
Galactaric acid is a conjugate acid of a galactarate(1-) and a galactaric acid anion.

CAS: 526-99-8
European Community (EC) Number: 208-404-0

IUPAC Name: (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid

Molecular Formula: C6H10O8
Molecular Weight: 210.14 g/mol

Mucic acid, C6H10O8 or HOOC-(CHOH)4-COOH (galactaric acid or meso-galactaric acid) is an aldaric acid obtained by nitric acid oxidation of galactose or galactose-containing compounds such as lactose, dulcite, quercite, and most varieties of gum.

Galactaric acid forms a crystalline powder, which melts at 210–230 °C.
Galactaric acid is insoluble in alcohol, and nearly insoluble in cold water.
Due to the symmetry in the molecule, Galactaric acid is optically inactive even though it has chiral carbon atoms (i.e., it is a meso compound).

When heated with pyridine to 140 °C, Galactaric acid is converted into allomucic acid.
When digested with fuming hydrochloric acid for some time it is converted into αα′ furfural dicarboxylic acid while on heating with barium sulfide it is transformed into α-thiophene 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.

Galactaric acid can be used to replace tartaric acid in self-raising flour or fizzies.

Galactaric acid has been used as a precursor of adipic acid in the way to nylon by a rhenium-catalyzed deoxydehydration reaction.

Galactaric acid has been used as a precursor of Taxol in Nicolaou Taxol total synthesis (1994).

Experimental Properties

Physical Description: Solid; Faintly beige powder
Color / Form: CRYSTALLINE POWDER
Melting Point: 220 - 225 °C
Solubility: ACICULAR CRYSTALS; SOL IN WATER /AMMONIUM SALT/

Galactaric acid is a monosaccharide that has been found in grape musts and wine and an oxidized form of galacturonic acid.
Galactaric acid (5-10 µM) increases mRNA expression of Runx2 in C3H/10T1/2 mouse mesenchymal stem cells.
Galactaric acid increases alkaline phosphatase (ALP) levels in, and mineralization of, C3H/10T1/2 cells when used in combination with gelatin as a coating on a 3D-poly (lactic acid) (PLA) scaffold at concentrations ranging from 10 to 20 µM.

Galactaric (mucic) acid is a symmetrical six carbon diacid which can be produced by oxidation of galactose with nitric acid, electrolytic oxidation of D-galacturonate or microbial conversion of D-galacturonate.
Both salts and the free acid of galactarate have relatively low solubility, which may create challenges for a microbial host.
Galactaric acid was most soluble at pH values around 4.7 in the presence of ammonium or sodium ions and less soluble in the presence of potassium ions.
Solubility increased with increasing temperature.
Production of galactaric acid by Trichoderma reesei D-161646 was dependent on temperature, pH and medium composition, being best at pH 4 and 35 °C.
Up to 20 g L-1 galactaric acid were produced from D-galacturonate using a fed-batch strategy with lactose as co-substrate and both ammonium and yeast extract as nitrogen sources.
Crystals of galactaric acid were observed to form in the broth of some fermentations.

Galactaric acid is a metal chelate that stimulates the metabolism of carbohydrates, fats and proteins.
Galactaric acid also plays a role in the production of energy in the body.
Galactaric acid has been shown to have a protective effect against infectious diseases, as it activates toll-like receptor 2 (TLR2) and TLR4, which are molecules involved in innate immunity.
Galactaric acid has been shown to protect against influenza virus infection by increasing the expression of interferon-gamma (IFN-γ) and IL-12, which are cytokines that inhibit viral replication.
Galactaric acid can be used as a fluorescence probe for detection of polymorphonuclear leucocytes in blood samples.

SYNONYMS:

mucic acid
galactaric acid
526-99-8
Saccharolactic acid
(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Galactosaccharic acid
D-Galactaric acid
galactarate
Schleimsaure
D-galactarate
Tetrahydroxyadipic acid
meso-galactaric acid
MFCD00004239
E149J5OTIF
(2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid
DTXSID7048740
CHEBI:30852
MUCICACID
2R,3S,4R,5S-tetrahydroxy-hexanedioic acid
DTXCID0028666
2,3,4,5-Tetrahydroxyhexanedioic acid
CAS-526-99-8
Schleimsaure [German]
UNII-E149J5OTIF
Galactarsaeure
Galaktarsaeure
Mucinsaeure
Saccharolactate
Schleimsaeure
acido mucico
hexaric acid
d-Zuckersaure
NSC-8127
Galactosaccharate
acido galactarico
(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioate
HSDB 2116
D-Mucic acid
NCGC00096080-01
NSC 8127
EINECS 208-404-0
MUCILIANCE
Mucic acid, 97%
Mucic acid, 98%
ORISTAR MCA
BRN 1728117
AI3-06294
AI3-19582
Tetrahydroxyhexanedioic acid
SCHEMBL5901
GALACTARIC ACID [MI]
mucic acid (galactaric acid)
4-03-00-01292 (Beilstein Handbook Reference)
GALACTARIC ACID [HSDB]
GALACTARIC ACID [INCI]
CHEMBL1232958
DSLZVSRJTYRBFB-DUHBMQHGSA-N
2,3,4,5-Tetrahydroxyadipic Acid
GALACTARIC ACID, (+/-)-
Tox21_113190
BDBM50346168
LMFA01170107
AKOS016009395
Tox21_113190_1
CS-W015126
HY-W014410
NCGC00344532-01
AS-35302
M0466
S3964
C00879
EN300-128455
A870928
Q424916
5E407223-AAEF-4D79-BCED-63F0DECB8CE2
W-109551
(R)-3-(pyrrolidin-2-ylethynyl)pyridine hemigalactarate
GAE