WO2005107385A2 - Method to produce novel carbohydrate-oxalic complex - Google Patents

Method to produce novel carbohydrate-oxalic complex Download PDF

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Publication number
WO2005107385A2
WO2005107385A2 PCT/US2005/010970 US2005010970W WO2005107385A2 WO 2005107385 A2 WO2005107385 A2 WO 2005107385A2 US 2005010970 W US2005010970 W US 2005010970W WO 2005107385 A2 WO2005107385 A2 WO 2005107385A2
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Prior art keywords
oxalic
complex
carbohydrate
oxalic complex
lactose
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PCT/US2005/010970
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French (fr)
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WO2005107385A3 (en
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Hsin Kuo Chu
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Hsin Kuo Chu
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Publication of WO2005107385A2 publication Critical patent/WO2005107385A2/en
Publication of WO2005107385A3 publication Critical patent/WO2005107385A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids

Definitions

  • the present invention relates generally to process for the production of carbohydrate-oxalic compounds, such as adding oxalic acid to the milk, and to the carbohydrate compounds.
  • This invention relates to a process for the production of carbohydrate-oxalic complex compounds by chemically reacting an oxalic acid with a carbohydrate compounds mixture at room temperature while agitated, thereby producing carbohydrate-oxalic complex compound.
  • carbohydrate compounds may be used in this process such as lactose, sucrose, maltose, N-acetyl-D-glucosame, D(L)-fructose, D(L)-glucose, D(L)-galactose, D(L)-mannose, D(L)-allose, D(L)-altrose, D(L)-gulose, D(L)-idose and D(L)-talose, lactose in milk, sucrose, fructose and glucose in fruit juice. Will produced by this method, such as adding oxalic acid to a solution to produce carbohydrate-oxalic complex compounds.
  • FIG. 1 depicts LC-MS, oxalic acid (MW 90) is chemically reacted with lactose(MW 342) to form lactose-oxalic complex(MW 432).
  • FIG. 2 depicts LC-MS results of milk.
  • FIG.3 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with lactose that is contained in the milk to form a lactose-oxalic complex (MW 432).
  • FIG. 4 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with sucrose(MW 342) to form sucrose-oxalic complex(MW 432).
  • FIG. 5 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with N-acetyl-D-glucosame (MW 221) to form N-acetyl-D-glucosame-oxalic complex(MW 311).
  • FIG.6 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with D-glucose(MW 180) to form D-glucose-oxalic complex(MW270).
  • FIG. 7 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with D-galatose(MW 180) to form D-galatose-oxalic complex(MW 270).
  • FIG. 8 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with D-mannose(MW 180) to form D-mannose-oxalic complex(MW 270).
  • sucrose dissolved in 200ml of water to produce an aqueous solution of sucrose.
  • oxalic acid is added slowly to the solution of sucrose, thereby producing sucrose-oxalic complex.
  • EXAMPLE 5 About 1 mole of D-galactose dissolved in 200ml of water to produce an aqueous solution of D- galactose. About 1 mole of oxalic acid is added slowly to the solution of D-galactose, thereby producing D-galactose-oxalic complex.
  • D-fructose dissolved in 200ml of water to produce an aqueous solution of D.L- fructose.
  • oxalic acid is added slowly to the solution of D-fructose, thereby producing D-fructose-oxalic complex.
  • N-acetyl-D-glucosame dissolved in 200ml of water to produce an aqueous solution of N-acetyl-D-glucosame.
  • About 1 mole of oxalic acid is added slowly to the solution of N-acetyl-D-glucosame, thereby producing N-acetyl-D-glucosame-oxalic complex.
  • oxalic acid About 2.5 grams of oxalic acid is slowly added to the 200ml of milk that is contained about 4.8% lactose. The oxalic acid is chemically reacted with lactose to producing lactose-oxalic complex.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Saccharide Compounds (AREA)

Abstract

Carbohydrate compounds are chemically reacted with an oxalic acid to form carbohydrate-oxalic complex. The lactose in the milk is chemically reacted with an oxalic acid to form a carbohydrate-oxalic complex.

Description

METHOD TO PRODUCE NOVEL CARBOHYDRATE-OXALIC COMPLEX
FIELD OF THE INVENTION The present invention relates generally to process for the production of carbohydrate-oxalic compounds, such as adding oxalic acid to the milk, and to the carbohydrate compounds.
SUMMARY OF THE INVENTION I have discovered the oxalic acid will react chemically with carbohydrate compounds at the temperature 0° to 100° C temperatures to produce carbohydrate-oxalic complex when 1 : 1 mol ratio is used.
DETAILED DESCRIPTION This invention relates to a process for the production of carbohydrate-oxalic complex compounds by chemically reacting an oxalic acid with a carbohydrate compounds mixture at room temperature while agitated, thereby producing carbohydrate-oxalic complex compound. Various carbohydrate compounds may be used in this process such as lactose, sucrose, maltose, N-acetyl-D-glucosame, D(L)-fructose, D(L)-glucose, D(L)-galactose, D(L)-mannose, D(L)-allose, D(L)-altrose, D(L)-gulose, D(L)-idose and D(L)-talose, lactose in milk, sucrose, fructose and glucose in fruit juice. Will produced by this method, such as adding oxalic acid to a solution to produce carbohydrate-oxalic complex compounds. References
1. Hassan S. El Khadem, Carbohydrate Chemistry, Monosacharides and their oligomers.
2. Peter M. Collins and Robert J. Ferrier, Monosacharides, their Chemistry and Their Role in Natural Products. John Wiley & Sons, 1995.
3. John F. Kennedy, Carbohydrate Chemistry, Clarendon Press, Oxford, 1988.
4. P. M. Collins, Carbohydrates-Dictionaries, Chapman and Hall Ltd., 1987.
5. Haruo Ogura, Akira Hasegawa and Tetsuo Suami, Carbohydrates-Synthetic methods and applications in Medicinal Chemistry, Kodanoha Ltd., Tokyo, 1992.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 depicts LC-MS, oxalic acid (MW 90) is chemically reacted with lactose(MW 342) to form lactose-oxalic complex(MW 432).
FIG. 2 depicts LC-MS results of milk.
FIG.3 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with lactose that is contained in the milk to form a lactose-oxalic complex (MW 432).
FIG. 4 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with sucrose(MW 342) to form sucrose-oxalic complex(MW 432).
FIG. 5 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with N-acetyl-D-glucosame (MW 221) to form N-acetyl-D-glucosame-oxalic complex(MW 311).
FIG.6 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with D-glucose(MW 180) to form D-glucose-oxalic complex(MW270).
FIG. 7 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with D-galatose(MW 180) to form D-galatose-oxalic complex(MW 270).
FIG. 8 depicts LC-MS, oxalic acid(MW 90) is chemically reacted with D-mannose(MW 180) to form D-mannose-oxalic complex(MW 270). DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples describe certain preferred embodiments of the processes which may, of course. Be varied as described above with similar results.
EXAMPLE 1.
About 1 mole of lactose dissolved in 200ml of water to produce an aqueous solution of lactose. About 1 mole of oxalic acid is added slowly to the solution of lactose , thereby producing lactose-oxalic complex.
EXAMPLE 2.
About 1 mole of sucrose dissolved in 200ml of water to produce an aqueous solution of sucrose. About 1 mole of oxalic acid is added slowly to the solution of sucrose, thereby producing sucrose-oxalic complex.
EXAMPLE 3
About 1 mole of D-glucose dissolved in 200ml of water to produce an aqueous solution of D- glucose. About 1 mole oxalic acid is added slowly to the solution of D-glucose, thereby producing D-glucose-oxalic complex.
EXAMPLE 4
About 1 mole of D-mannose dissolved in 200ml of water to produce an aqueous solution of D.L- mannose. About 1 mole of oxalic acid is added slowly to the solution of D-mannose, thereby producing D-mannose-oxalic complex.
EXAMPLE 5 About 1 mole of D-galactose dissolved in 200ml of water to produce an aqueous solution of D- galactose. About 1 mole of oxalic acid is added slowly to the solution of D-galactose, thereby producing D-galactose-oxalic complex.
EXAMPLE 6
About 1 mole of D-fructose dissolved in 200ml of water to produce an aqueous solution of D.L- fructose. About 1 mole of oxalic acid is added slowly to the solution of D-fructose, thereby producing D-fructose-oxalic complex.
EXAMPLE 7
About 1 mole of N-acetyl-D-glucosame dissolved in 200ml of water to produce an aqueous solution of N-acetyl-D-glucosame. About 1 mole of oxalic acid is added slowly to the solution of N-acetyl-D-glucosame, thereby producing N-acetyl-D-glucosame-oxalic complex.
EXAMPLE 8
About 2.5 grams of oxalic acid is slowly added to the 200ml of milk that is contained about 4.8% lactose. The oxalic acid is chemically reacted with lactose to producing lactose-oxalic complex.

Claims

WHAT IS CLAIMED IS: 1. The process for the production of carbohydrate oxalic complex by the following steps. a. Mixing about equal parts by mole(s) of oxalic acid (C2H2O4, MW 90) and carbohydrate compounds. b. Mixture at room temperature while agitating thereby. c. Producing a carbohydrate-oxalic complex.
2. The method of claim 1. wherein the carbohydrate compounds including: lactose (C12H22O11, MW 342), sucrose (Ci2H22θn,MW 342), maltose (Ci2H22θii,MW 342), cellobiose (C12H22O1LMW 342), N-acetyl-D-glucosame (CsHisOeN, MW 221),
D(L)- fructose (CeHnOe, MW 180), D(L)-glucose (C6H12O6, MW 180), D(L)- galactose (C6H12O6, MW 180), D(L)-mannose (CβHuOδ, MW 180), D(L)-allose (C6H12O6,
MW 180), D(L)-altrose (C6H12O6, MW 180), D(L)-gulose (CeHnOe, MW 180),
D(L)-idose (CβHnOβ, MW 180) and D(L)-talose (C6H12O6, MW 180).
3. The method of claim 1. wherein the carbohydrate compounds including lactose in the milk.
4. The method of claim 1. wherein the carbohydrate compounds including sucrose, fructose, glucose in the fruit juice.
5. The method of claim 1 including the further steps of: a. Adding an oxalic acid in the ratio of 1 millimol to 1 mol to each mol of the carbohydrate. b. Mixing between 0° to 100° C while agitating, thereby. c. Producing a carbohydrate-oxalic complex.
6. The process for the production of carbohydrate-oxalic complex by the following steps. a. Providing oxalic acid (MW 90) b. The carbohydrates including: lactose (C12H22O11, MW 342), sucrose (C12H22O11, MW 342), maltose (C12H22O11, MW 342), cellobiose (C12H22O11. W 342), N-acetyl-D-glucosame (CsHisOόN, MW 221), D(L fructose (CόHπOe, MW 80), D(L)-glucose (C6H12O6, MW 180), D(L)- galactose CeH Oό, MW 180), D(L)-mannose (C BnOά, MW 180), D(L)-allose (CβHnOβ, MW 180), D(L)-altrose (CeHi2θ6, MW 180), D(L)-gulose (CβH Oδ, MW 180), D(L)-idose (CeHi∑Oδ, MW 180) and D(L)-talose (CeH Oβ, MW 180).
7. The process for the production of lactose-oxalic complex (C14H24O15, MW 432), sucrose-oxalic complex (C14H24O1S, MW 432), maltose-oxalic complex (C14H24O15.MW 432), cellobiose-oxalic complex (CuHatOis. MW 432), N-acetyl-D-glucosame-oxalic complex (CioHπOioN, MW 31 1), D(L)- fructose-oxalic complex (CβHwOio, MW 270), D(L)-glucose-oxalic complex (CSHMOIO, MW 270), D(L)-GaIactose-oxalic complex (CSHMOIO, M 270), D(L)-mannose- oxalic complex (CSHHOIO, MW 270), D(L)-allose-oxalic complex (CSHMOIO, MW 270) D(L)-altrose-oxaiic complex (CSHMOIO, MW 270), D(L)-gulose-oxalic complex (CSHMOIO, MW 270), D(L)-idose-oxalic complex (CβHuOio, MW 270) and D(L)-talose-oxalic complex
Figure imgf000007_0001
PCT/US2005/010970 2004-04-27 2005-03-31 Method to produce novel carbohydrate-oxalic complex WO2005107385A2 (en)

Applications Claiming Priority (2)

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US70072804A 2004-04-27 2004-04-27
US10/700,728 2004-04-27

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WO2005107385A3 WO2005107385A3 (en) 2007-04-19

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862121A (en) * 1970-11-13 1975-01-21 Ciba Geigy Corp Ether and ester substituted d-glycofuranoside compounds
US4683074A (en) * 1985-04-26 1987-07-28 A. E. Staley Manufacturing Company Stability and compatibility of glycosides in acid systems

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862121A (en) * 1970-11-13 1975-01-21 Ciba Geigy Corp Ether and ester substituted d-glycofuranoside compounds
US4683074A (en) * 1985-04-26 1987-07-28 A. E. Staley Manufacturing Company Stability and compatibility of glycosides in acid systems

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