87-81-0 Usage
Description
D-tagatose is a carbohydrate occurring in small amounts in several foods. The
solubility in water is approximately 580 g/L at room temperature. As a ketohexose,
tagatose reacts in foods in browning reactions like other ketohexoses, for
example, fructose.
Tagatose is, depending on the concentration, approximately 92 % as sweet as
sucrose and noncariogenic. The caloric value of tagatose is generally set to
1.5 kcal/g.
In the European Union, tagatose is approved as a novel food. In the United
States, tagatose has GRAS status and it is also approved in many other countries.
Chemical Properties
Different sources of media describe the Chemical Properties of 87-81-0 differently. You can refer to the following data:
1. Tagatose is a white, anhydrous crystalline solid. It is a carbohydrate,
a ketohexose, an epimer of D-fructose inverted at C-4. It can exist in
several tautomeric forms.
2. white to off-white crystalline powder
Uses
Different sources of media describe the Uses of 87-81-0 differently. You can refer to the following data:
1. A monosaccharide (hexose) that can be used as a low-calorie sweetener, as an intermediate for synthesis of other optically active compounds, and as an additive in detergent, cosmetic, and pharmaceutical formulation.
2. D-(-)-Tagatose has been used as a carbohydrates for fermentation. It has also been used as one of the standards to confirm the identity of majority of the metabolites selected by least absolute shrinkage and selection operator (LASSO).
3. D-tagatose is a compound useful in organic synthesis.
Production Methods
Tagatose is obtained from D-galactose by isomerization under
alkaline conditions in the presence of calcium.
Biotechnological Production
Tagatose is produced from galactose, which can be obtained by enzymatic
hydrolysis of lactose, the main carbohydrate of milk. Galactose is separated from
glucose by chromatography and either isomerized by treatment with calcium
hydroxide, subsequent precipitation of calcium carbonate with carbon dioxide,
filtration, demineralization with ion exchangers and crystallization [15], or converted
enzymatically.
Especially high conversion rates of 96.4 % were obtained with an enzyme
extract of an engineered E. coli, and of 60 % at 95 C for A. flavithermus in
the presence of borate. Conversion rates of 58 % were reported for an enzyme
obtained from a mutant of G. thermodenitrificans [100], of 54 % at 60 C for a
recombinant enzyme of Thermus sp. expressed in E. coli, and of more than
50 % at 75 C for E. coli containing an enzyme of A. cellulolytics.
Immobilized enzymes or whole cells were used for practical applications. In
some studies, high yields and productivities were achieved.
Immobilized L-arabinose isomerase in calcium alginate produced 145 g/L of
tagatose with 48 % conversion of galactose and a productivity of 54 g/Lh in a
packed-bed reactor. An enzyme of T. mathranii immobilized in calcium alginate had its optimum at 75 C with a conversion rate of 43.9 % and a
productivity up to 10 g/Lh with, however, lower conversion. After incubation of
the resulting syrup with S. cerevisiae, purities above 95 % were achieved. The
enzyme of T. neapolitana immobilized on chitopearl beds gave a tagatose
concentration of 138 g/L at 70 C.
Lactobacillus fermentum immobilized in calcium alginate had a temperature
optimum of 65 C. A conversion rate of 60 % and a productivity of 11.1 g/Lh were
obtained in a packed-bed reactor after addition of borate.
Direct production of tagatose in yogurt was possible by expressing the enzyme
of B. stearothermophilus in Lactobacillus bulgaricus and Streptococcus thermophilus.
Pharmaceutical Applications
Tagatose is used as a sweetening agent in beverages, foods, and
pharmaceutical applications. A 10% solution of tagatose is about
92% as sweet as a 10% sucrose solution. It is a low-calorie sugar
with approximately 38% of the calories of sucrose per gram. It
occurs naturally in low levels in milk products. Like other sugars
(fructose, glucose, sucrose), it is also used as a bulk sweetener,
humectant, texturizer, and stabilizer, and may be used in dietetic
foods with a low glycemic index.
Biological Activity
D-Tagatose, a ketohexose acts as a low-calorie functional sweetener. Tagatose can be used as a preservative in cosmetic, detergent and pharmaceutical formulations.Tagatose is also used in diet soft drinks, chewing gum, frozen yogurt and non-fat ice cream.Potential sugar substitute rarely found in nature. Produced using a biotransformation method with L-arabinose isomerase as the biocatalyst and D-galactose as the substrate.
Side effects
Some human trials of D-tagatose have found that doses of 30 grams or more cause gastrointestinal side effects like flatulence, diarrhea, nausea, and vomiting.However, only a minority of people appear to be affected, and mostly only with light to moderate symptom severity.The GI side effects of D-tagatose seem to be unpleasant but harmless. They’re may be due to osmotic (water-retaining) effects of high D-tagatose doses moving through your intestines.D-tagatose may interact with some prescription drugs, especially blood sugar lowering drugs, and could cause hypoglycemia (dangerously low blood sugar levels).And in people with diabetes or a history of kidney stones, temporary rises in uric acid blood levels caused by high dose D-tagatose may be an issue.
Safety
Tagatose is safe for use in food and beverages. It has been used in
pharmaceutical products.
storage
Tagatose is stable under pH conditions typically encountered in
foods (pH>3). It is a reducing sugar and undergoes the Maillard
reaction.
Tagatose is stable under typical storage conditions. It caramelizes
at elevated temperature.
Purification Methods
Crystallise D(-)-tagatose from EtOH/H2O (6:1). It mutarotates from [] 22D +2o (2minutes) to –5.0o (30minutes) (c 4, H2O). The phenylosazone crystallises from aqueous EtOH with m 185-187o(dec), and [] 23D +47o (c 0.82, 2-methoxyethanol). [Totton & Lardy J Am Chem Soc 71 3076 1949, Gorin et al. Canad J Chem 33 1116 1955, Reichestein & Bossard Helv Chem Acta 17 753 1934, Wolfrom & Bennett J Org Chem 30 1284 1965, Beilstein 1 IV 4414.] In D2O at 27o 1H NMR showed the following ratios: -pyranose (79), -pyranose (16), -furanose (1) and -furanose (4) [Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972].
Incompatibilities
A Maillard-type condensation reaction is likely to occur between
tagatose and compounds with a primary amine group to form
brown or yellow-brown colored Amidori compounds. Reducing
sugars will also interact with secondary amines to form an imine,
but without any accompanying yellow-brown discoloration.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database
(oral and rectal solutions).
Check Digit Verification of cas no
The CAS Registry Mumber 87-81-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 87-81:
(4*8)+(3*7)+(2*8)+(1*1)=70
70 % 10 = 0
So 87-81-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5+,6?/m1/s1
87-81-0Relevant articles and documents
Few-Unit-Cell MFI Zeolite Synthesized using a Simple Di-quaternary Ammonium Structure-Directing Agent
Abeykoon, Milinda,Al-Thabaiti, Shaeel,Bell, Alexis T.,Boscoboinik, J. Anibal,Dai, Heng,Dauenhauer, Paul,Dorneles de Mello, Matheus,Duan, Xuekui,Ghosh, Supriya,Kamaluddin, Huda Sharbini,Khan, Zaheer,Kumar, Gaurav,Li, Xinyu,Lu, Peng,Luo, Tianyi,Mkhoyan, K. Andre,Narasimharao, Katabathini,Qi, Liang,Rimer, Jeffrey D.,Tsapatsis, Michael
supporting information, p. 19214 - 19221 (2021/08/09)
Synthesis of a pentasil-type zeolite with ultra-small few-unit-cell crystalline domains, which we call FDP (few-unit-cell crystalline domain pentasil), is reported. FDP is made using bis-1,5(tributyl ammonium) pentamethylene cations as structure directing agent (SDA). This di-quaternary ammonium SDA combines butyl ammonium, in place of the one commonly used for MFI synthesis, propyl ammonium, and a five-carbon nitrogen-connecting chain, in place of the six-carbon connecting chain SDAs that are known to fit well within the MFI pores. X-ray diffraction analysis and electron microscopy imaging of FDP indicate ca. 10 nm crystalline domains organized in hierarchical micro-/meso-porous aggregates exhibiting mesoscopic order with an aggregate particle size up to ca. 5 μm. Al and Sn can be incorporated into the FDP zeolite framework to produce active and selective methanol-to-hydrocarbon and glucose isomerization catalysts, respectively.
L-Xylo-3-hexulose, a new rare sugar produced by the action of acetic acid bacteria on galactitol, an exception to Bertrand Hudson's rule
Xu, Yirong,Chi, Ping,Lv, Jiyang,Bilal, Muhammad,Cheng, Hairong
, (2020/10/02)
Background: In acetic acid bacteria such as Gluconobacter oxydans or Gluconobacter cerinus, pyrroloquinoline quinone (PQQ) in the periplasm serves as the redox cofactor for several membrane-bound dehydrogenases that oxidize polyhydric alcohols to rare sugars, which can be used as a healthy alternative for traditional sugars and sweeteners. These oxidation reactions obey the generally accepted Bertrand Hudson's rule, in which only the polyhydric alcohols that possess cis D-erythro hydroxyl groups can be oxidized to 2-ketoses using PQQ as a cofactor, while the polyhydric alcohols excluding cis D-erythro hydroxyl groups ruled out oxidation by PQQ-dependent membrane-bound dehydrogenases. Methods: Membrane fractions of G. oxydans were prepared and used as a cell-free catalyst to oxidize galactitol, with or without PQQ as a cofactor. Results: In this study, we reported an interesting oxidation reaction that the polyhydric alcohols galactitol (dulcitol), which do not possess cis D-erythro hydroxyl groups, can be oxidized by PQQ-dependent membrane-bound dehydrogenase(s) of acetic acid bacteria at the C-3 and C-5 hydroxyl groups to produce rare sugars L-xylo-3-hexulose and D-tagatose. Conclusions: This reaction may represent an exception to Bertrand Hudson's rule. General significance: Bertrand Hudson's rule is a well-known theory in polyhydric alcohols oxidation by PQQ-dependent membrane-bound dehydrogenase in acetic acid bacteria. In this study, galactitol oxidation by a PQQ-dependent membrane-bound dehydrogenase represents an exception to the Bertrand Hudson's rule. Further identification of the associated enzymes and deciphering the explicit enzymatic mechanism will prove this theory.
Method for preparing lactic acid through catalytically converting carbohydrate
-
Paragraph 0029-0040, (2020/11/01)
The invention relates to a method for preparing lactic acid through catalytically converting carbohydrate, and in particular, relates to a process for preparing lactic acid by catalytically convertingcarbohydrate under hydrothermal conditions. The method disclosed by the invention is characterized by specifically comprising the following steps: 1) adding carbohydrate and a catalyst into a closedhigh-pressure reaction kettle, and then adding pure water for mixing; 2) introducing nitrogen into the high-pressure reaction kettle to discharge air, introducing nitrogen of 2 MPa, stirring and heating to 160-300 DEG C, and carrying out reaction for 10-120 minutes; 3) putting the high-pressure reaction kettle in an ice-water bath, and cooling to room temperature; and 4) filtering the solution through a microporous filtering membrane to obtain the target product. The method can realize high conversion rate of carbohydrate and high yield of lactic acid, and has the advantages of less catalyst consumption, good circularity, small corrosion to reaction equipment and the like.