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D-Fructose

PubChem CID
2723872
Structure
D-Fructose_small.png
D-Fructose_3D_Structure.png
Molecular Formula
Synonyms
  • fructose
  • D-fructopyranose
  • D-fructose
  • fructopyranose
  • fructopyranoside
Molecular Weight
180.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-04
Description
D-fructopyranose is a fructopyranose having D-configuration. It has a role as a sweetening agent. It is a fructopyranose, a D-fructose and a cyclic hemiketal.
D-Fructose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
D-Fructose has been reported in Maclura pomifera, Rehmannia glutinosa, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
D-Fructose.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Fru
LINUCS
[][D-Frup]{}
IUPAC
D-arabino-hex-2-ulopyranose

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

LKDRXBCSQODPBY-VRPWFDPXSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1[C@H]([C@H]([C@@H](C(O1)(CO)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C6H12O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)
C6H12O6

3.3 Other Identifiers

3.3.1 CAS

57-48-7
7660-25-5
30237-26-4

3.3.2 Deprecated CAS

10597-68-9, 149014-33-5, 196419-06-4, 3812-57-5, 69-67-0

3.3.3 European Community (EC) Number

3.3.4 ChEBI ID

3.3.5 ChEMBL ID

3.3.6 DrugBank ID

3.3.7 ICSC Number

3.3.8 KEGG ID

3.3.9 Metabolomics Workbench ID

3.3.10 NCI Thesaurus Code

3.3.11 Nikkaji Number

3.3.12 RXCUI

3.3.13 Wikidata

3.3.14 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Apir Levulosa
  • Fleboplast Levulosa
  • Fructose
  • Levulosa
  • Levulosa Baxter
  • Levulosa Braun
  • Levulosa Grifols
  • Levulosa Ibys
  • Levulosa Ife
  • Levulosa Mein
  • Levulosa, Apir
  • Levulosa, Fleboplast
  • Levulosado Bieffe Medit
  • Levulosado Braun
  • Levulosado Vitulia
  • Levulose
  • Plast Apyr Levulosa Mein

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
180.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
180.06338810 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
180.06338810 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
110Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
162
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Physical Description

Liquid
White solid; [ICSC] Colorless crystalline solid; [Sigma-Aldrich MSDS]
WHITE CRYSTALS OR POWDER.

4.2.2 Color / Form

CLEAR COLORLESS LIQUID IN WATER
National Research Council. Specifications and Criteria for Biochemical Compounds. 3rd ed. Washington, DC: National Academy of Sciences, 1972., p. 38
COLORLESS CRYSTALS OR AS A WHITE, CRYSTALLINE OR GRANULAR POWDER
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964
White crystals
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 520

4.2.3 Odor

ODORLESS
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964

4.2.4 Taste

SWEET
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964

4.2.5 Solubility

Solubility in water at 20 °C: good

4.2.6 Autoignition Temperature

360 °C

4.2.7 Decomposition

103-105 °C

4.2.8 Collision Cross Section

135 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine]
141.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
141.93 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
141.4 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

4.2.9 Other Experimental Properties

Orthorhombic, bisphenodial prisms from alc, dec 103-105 °C. Sweetest of the sugars. Shows mutarotation. Specific optical rotation: -132 deg to -92 deg (c=2) @ 20 °C/D. Rapid and anomalous mutarotation involve pyranose-furanose interconversion. The final mutarotation value is obtained instantly in the presence of hydroxyl ions. pKa= 12.06 @ 18 °C. Freely sol in water. One gram dissolves in 15 ml alc, in 14 ml methanol. Slightly sol in cold, freely in hot acetone; sol in pyridine, ethylamine, methylamine. /D-Fructose/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 724
MP: 103 °C (dec); density: 1.60 @ 20 °C/4 °C /beta-levulose/
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-167

4.3 Chemical Classes

Biological Agents -> Monosaccharides and Derivatives

4.3.1 Cosmetics

Cosmetic ingredients (Fructose) -> CIR (Cosmetic Ingredient Review)
Humectant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4.3.2 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
179.0561121
Instrument
Agilent qTOF 6545
Instrument Type
LC-ESI-QTOF
Ionization Mode
negative
Collision Energy
40 eV
Top 5 Peaks

59.01472 100

59.02263 67.70

43.01821 17.40

41.01209 17

59.03278 17

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
179.0561121
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
negative
Collision Energy
HCD (NCE 20-30-40%)
Top 5 Peaks

71.01385 100

59.0137 99.40

89.02445 83.70

113.02463 15.10

101.02439 11.60

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Thumbnail

5.3 Other Spectra

LOSS OF WT ON DRYING NOT MORE THAN 0.1%; ASH: NOT MORE THAN 0.05%; HEAVY METALS (AS COPPER) NOT MORE THAN 10 PPM; IRON 5 PPM; AS 0.5 PPM
National Research Council. Specifications and Criteria for Biochemical Compounds. 3rd ed. Washington, DC: National Academy of Sciences, 1972., p. 38

7 Chemical Vendors

8 Drug and Medication Information

8.1 FDA National Drug Code Directory

8.2 Drug Labels

Drug and label
Active ingredient and drug

8.3 Clinical Trials

8.3.1 ClinicalTrials.gov

8.3.2 NIPH Clinical Trials Search of Japan

8.4 Therapeutic Uses

...IT IS UTILIZED BY DIABETIC PATIENTS WITH KETOACIDOSIS...MAY BE USEFUL IN EARLY MANAGEMENT OF THIS COMPLICATION OF DIABETES MELLITUS.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 769
MEDICATION (VET): AS A SUBSTITUTE FOR GLUCOSE IN PARENTERAL FLUIDS SINCE IT DOES NOT EXCEED RENAL THRESHOLD AS READILY. THUS, 10% SOLN CAN BE USED INSTEAD OF 5% GLUCOSE PROVIDING MORE TOTAL CALORIES PER ML, & THIS ACCOUNTS FOR ITS USE IN ACETONEMIA THERAPY IN ADULT CATTLE.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 229
FRUCTOSE SOLN, LIKE THOSE OF DEXTROSE, ARE EMPLOYED TO REPLACE OR SUPPLEMENT ORAL CONSUMPTION OF FOOD OR WATER IN ORDER TO PROVIDE CALORIES REQUIRED FOR METABOLIC NEEDS, TO SUPPLY BODY WATER, TO SPARE BODY PROTEINS, TO LOWER PRODN OF EXCESS KETONES BY LIVER, & TO SPARE LOSS OF ELECTROLYTES.
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:20
DENTAL ASPECTS OF CONSUMPTION OF FRUCTOSE DIETS RESULTED IN REDUCTION OF INCIDENCE OF DENTAL CARIES BY 30%.
MAKINEN KK; INT DENT J 26(1) 14 (1976)
For more Therapeutic Uses (Complete) data for FRUCTOSE (6 total), please visit the HSDB record page.

8.5 Drug Warnings

SUBCUTANEOUS ROUTE IS NOT RECOMMENDED, BECAUSE SUGARS GIVEN SC CAUSE ELECTROLYTE DISTORTIONS, WHICH OCCASIONALLY MAY BE SEVERE.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964
FRUCTOSE IS NONTOXIC BUT SOLN SHOULD BE ADMIN SLOWLY. IT DECOMPOSES IN ALKALINE SOLN & THUS SUBSTANCES WHICH WOULD RAISE PH ABOVE 7 SHOULD NOT BE ADDED. CALCIUM & BARIUM FORM INSOL COMPLEXES WITH FRUCTOSE WHEN PH EXCEEDS 7 & ARE THUS INCOMPATIBLE. CLOUDY SOLN OF FRUCTOSE SHOULD NOT BE USED.
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:20

9 Agrochemical Information

9.1 Agrochemical Category

Pesticide active substances

9.2 EU Pesticides Data

Active Substance
fructose
Status
Approved [Reg. (EC) No 1107/2009]
Legislation
Reg. (EU) 2015/1392, Reg. (EU) No 540/2011

10 Pharmacology and Biochemistry

10.1 MeSH Pharmacological Classification

Sweetening Agents
Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) (See all compounds classified as Sweetening Agents.)

10.2 ATC Code

V - Various

V06 - General nutrients

V06D - Other nutrients

V06DC - Carbohydrates

V06DC02 - Fructose

10.3 Absorption, Distribution and Excretion

TWICE THE CONCN OF FRUCTOSE CAN BE INFUSED AT THE SAME RATE AS DEXTROSE WITH BETTER RETENTION AND LESS DISTURBANCE OF FLUID BALANCE.
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:20
...ADVANTAGES OF FRUCTOSE IS ITS RAPID REMOVAL FROM EXTRACELLULAR SPACE, & THEREFORE, URINARY EXCRETION IS MINIMIZED.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 769

10.4 Metabolism / Metabolites

IN ABSENCE OF GLUCOSE, FRUCTOSE IS PHOSPHORYLATED PERIPHERALLY BY HEXOKINASE TO FRUCTOSE-6-PHOSPHATE, &, ON ACCOUNT OF HIGH KM VALUE FOR FRUCTOSE & LOW KM VALUE FOR GLUCOSE, LATTER IS PREFERENTIALLY PHOSPHORYLATED BY THIS ENZYME IN PERIPHERAL TISSUES.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 171
ORAL FRUCTOSE IS OFTEN CONVERTED TO GLUCOSE IN INTESTINAL MUCOSA OF A NUMBER OF SPECIES, SUCH AS GUINEA PIG, HAMSTER, & DOG. NEWBORN PIGS & YOUNG CALVES UP TO 1 MO OF AGE CANNOT UTILIZE IT. SPECIES...WITH LOW GLUCOSE-6-PHOSPHATE DEHYDROGENASE & RELATED ENZYME DEFICIENCIES MAY HAVE DIFFICULTY IN METABOLIZING IT.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 229
FRUCTOSE IS MORE RAPIDLY METABOLIZED & MORE QUICKLY CONVERTED TO GLYCOGEN THAN IS DEXTROSE, & PRESENCE OF INSULIN IS NOT NECESSARY FOR THIS REACTION TO TAKE PLACE. WHEN...INJECTED LOWER LEVELS OF BLOOD SUGAR & LESS SPILLAGE RESULT THAN WHEN SIMILAR AMT OF DEXTROSE ARE GIVEN @ SAME RATE.
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:20

10.5 Biochemical Reactions

10.6 Transformations

11 Use and Manufacturing

11.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Fructose
Sources/Uses
Sweetest of the sugars found in fruits and honey; Added to ice cream to prevent sandiness; [Merck Index] Used as a preservative and as an intravenous infusion in parenteral feeding; [ChemIDplus] Used as an additive to food/foodstuffs and in pharmaceuticals; [IUCLID] Used as flavoring agent or adjuvant, formulation aid, nutritive sweetener, processing aid, solvent, stabilizer or thickener, and texturizer for foods; [FDA]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
MEDICATION (VET)
MEDICATION
To prevent sandiness in ice cream /D-Fructose/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 724
Therap cat: Fluid and nutrient replenisher, and ferric form as hematinic. /D-Fructose/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 724
For more Uses (Complete) data for FRUCTOSE (9 total), please visit the HSDB record page.

11.1.1 Use Classification

Cosmetics -> Humectant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

11.1.2 Household Products

Household & Commercial/Institutional Products

Information on 13 consumer products that contain Fructose in the following categories is provided:

• Inside the Home

• Personal Care

11.2 Methods of Manufacturing

ACTION OF IMMOBILIZED GLUCOSE ISOMERASE (DERIVED PRINCPLY FROM STREPTOMYCES SPECIES) ON DEXTROSE (FRUCTOSE AND HIGH FRUCTOSE (42%) CORN SYRUP); HYDROLYSIS OF INULIN (FRUCTOSE); HYDROLYSIS OF BEET SUGAR FOLLOWED BY LIME SEPARATION (FRUCTOSE)
SRI
Prepared by adding absolute alc to the syrup obtained from acid hydrolysis of inulin: Bates et al, Natl Bur Std (US), Circ C440, 399 (1942). Prepn from dextrose: Cantor, Hobbs, US patent 2,354,664 (1944 to Corn Prod Refining). From sucrose by enzymatic conversion: Koepsell et al, US patent 2,729,587 (1956 to USA). /D-Fructose/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 723
Hydrolysis of inulin; hydrolysis of beet sugar followed by lime separation; from cornstarch by enzymic or microbial action.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 520
Hydrolysis of sucrose produces a mixture of glucose and fructose, from which fructose can be separated by chromatography. /D-Fructose/
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA12 (89) 49
The saccharification of starch produces glucose, which can be isomerized with the aid of the enzyme glucose isomerase ... to "high-fructose corn syrup" HFCS ... . /D-Fructose/
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA12 (89) 50

11.3 Formulations / Preparations

FRUCTOSE INJECTION, NF, IS STERILE SOLN OF FRUCTOSE IN WATER...10% SOLN, PH 3.0-6.0.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 769
DOSAGE FORMS- INJECTION NF: 100 G/1000 ML; FRUCTOSE & SODIUM CHLORIDE INJECTION NF: 100 G (FRUCTOSE) & 9 G (SODIUM CHLORIDE)/1000 ML.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964
High-fructose corn syrups ... contain 42, 55 or 90% fructose on a dry weight basis
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V22 (80) 507
Crystalline fructose is essentially pure
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V22 (80) 510
For more Formulations/Preparations (Complete) data for FRUCTOSE (6 total), please visit the HSDB record page.

11.4 U.S. Production

Aggregated Product Volume

2019: 10,000,000 - <50,000,000 lb

2018: 10,000,000 - <50,000,000 lb

2017: 10,000,000 - <50,000,000 lb

2016: 10,000,000 - <50,000,000 lb

(1976) 9X10+11 G (HIGH FRUCTOSE CORN SYRUP-EST
SRI
(1980) 2.66X10+12 g /total indust distribution of high-fructose corn syrup/
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V22 (80) 506
(1980) 3.20X10+9 g /consumption of crystalline fructose/
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V22 (80) 510
World output of fructose syrup (fructose content of total solids >95%) is estimated at 25,000 t/a and of the crystalline product at 35,000 t/a. The market for crystalline fructose is predicted to be 100,000 t/a in the 1990s. /D-Fructose/
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA12 (89) 49

11.5 U.S. Imports

(1985) 1.95X10+9 g /levulose/
BUREAU OF THE CENSUS. U.S. IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1985 p.1-613

11.6 General Manufacturing Information

EPA TSCA Commercial Activity Status
D-Fructose: ACTIVE
HOMOGENEITY DETERMINED BY PAPER...& GAS-LIQUID CHROMOTOGRAPHY SYSTEMS...
National Research Council. Specifications and Criteria for Biochemical Compounds. 3rd ed. Washington, DC: National Academy of Sciences, 1972., p. 38
Fructose is crystallized on a large scale in either of two ways: by cooling an aqueous solution or by inducing precipitation from such a solution by adding organic solvents such as methanol or ethanol. /D-Fructose/
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA12 (89) 50
...CAN BE INFUSED IV IN HIGHER (TWICE) CONCN THAN DEXTROSE WITHOUT AS MUCH... PLASMA HYPERTONICITY; ALSO...SMALLER VOL OF WATER INFUSED, WHEN FRUCTOSE IS CONVERTED FROM BLOOD THERE IS LESS RESIDUAL HYDREMIA.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964

12 Identification

12.1 Analytic Laboratory Methods

ENZYMATIC METHOD IS A RAPID & SPECIFIC ASSAY FOR FRUCTOSE. /SPECTROPHOTOMETRY OR SPECTRUM-LINE PHOTOMETRY ARE ALSO/...SUITABLE FOR ACCURATE MEASUREMENTS @ 340, 334, OR 365 NM...
Bergmeyer, H.W. (ed.). Methods of Enzymatic Analysis. 2nd English ed. New York City: Academic Press, 1974., p. 1304
AOAC Method 956.63. Fructose in sugars and sirups. Chemical methods.
Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC: Association of Analytical Chemists, 1990, p. 1017
AOAC Method 932.15. Fructose in sugars and sirups. Jackson-Mathews modification of the Nyns selective method. /D-(-)-Fructose/
Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC: Association of Analytical Chemists, 1990, p. 1017

13 Safety and Hazards

13.1 Hazards Identification

13.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (203 of 203) of all reports. Pictograms displayed are for < 0.1% (0 of 203) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 203 of 203 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 203 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 203 of 203 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 203 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

13.1.2 Hazard Classes and Categories

Not Classified

13.1.3 Fire Hazards

Combustible. Finely dispersed particles form explosive mixtures in air.

13.1.4 Hazards Summary

May cause mechanical irritation; [ICSC] May cause irritation; [Sigma-Aldrich MSDS]

13.2 Safety and Hazard Properties

13.2.1 Physical Dangers

Dust explosion possible if in powder or granular form, mixed with air.

13.3 First Aid Measures

Inhalation First Aid
Fresh air, rest.
Skin First Aid
Rinse and then wash skin with water and soap.
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth.

13.4 Fire Fighting

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

13.5 Accidental Release Measures

13.5.1 Spillage Disposal

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

13.5.2 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

13.6 Handling and Storage

13.6.1 Safe Storage

Separated from strong oxidants.

13.7 Exposure Control and Personal Protection

13.7.1 Inhalation Risk

A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

13.7.2 Effects of Short Term Exposure

May cause mechanical irritation.

13.7.3 Preventions

Fire Prevention
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
Inhalation Prevention
Use local exhaust or breathing protection.
Eye Prevention
Wear safety goggles.
Ingestion Prevention
Do not eat, drink, or smoke during work.

13.8 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: D-Fructose
Status Regulation (EC)
Reg. (EU) 2015/1392, Reg. (EU) No 540/2011
New Zealand EPA Inventory of Chemical Status
Fructose: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
New Zealand EPA Inventory of Chemical Status
D-Fructose: Does not have an individual approval but may be used under an appropriate group standard

13.9 Other Safety Information

Chemical Assessment

IMAP assessments - D-Fructose: Environment tier I assessment

IMAP assessments - D-Fructose: Human health tier I assessment

14 Toxicity

14.1 Toxicological Information

14.1.1 Symptoms

Inhalation Exposure
Cough.
Eye Exposure
Redness. Pain.

14.1.2 Interactions

IN CONTROLLED STUDY OF PATIENTS WITH ACUTE ALCOHOLIC INTOXICATION, IV INFUSION OF LARGE DOSE...CAUSED SMALL BUT STATISTICALLY SIGNIFICANT INCR IN RATE OF FALL OF BLOOD ETHANOL LEVELS. ... USUAL EXPLANATION FOR THIS EFFECT OF FRUCTOSE... IS ENHANCEMENT OF ACTION OF ALC DEHYDROGENASE BY SUGAR ITSELF OR BY ONE OF ITS METABOLITES.
The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 623
REDUCTION IN MUTAGENICITY OF CIGARETTE SMOKE BY INTERACTION OF SMOKE CONDENSATES WITH ADDED FRUCTOSE.
SATO S ET AL; MUTAT RES 60 (2): 155 (1979)

14.1.3 Human Toxicity Excerpts

INFUSION OF FRUCTOSE HAS BEEN ASSOCIATED WITH INCREASED URIC ACID PRODUCTION & HYPERURICEMIA. IN PATIENTS WITH HEREDITARY FRUCTOSE INTOLERANCE (ALDOLASE DEFICIENCY), FRUCTOSE CAN CAUSE SEVERE REACTIONS (HYPOGLYCEMIA, NAUSEA, VOMITING, TREMORS, COMA, CONVULSIONS).
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 235
IV INFUSION OF FRUCTOSE DEPLETED HEPATIC ATP & TOTAL ADENOSINE PHOSPHATES IN HUMANS, THEREBY INTERFERING WITH VARIOUS ENERGY-DEPENDENT REACTIONS.
BODE JC ET AL; EUR J CLIN INVEST 3(5) 436 (1973)

14.1.4 Non-Human Toxicity Excerpts

IV INFUSION OF D-FRUCTOSE DEPLETED HEPATIC ATP & TOTAL ADENOSINE PHOSPHATES IN RATS, THEREBY INTERFERING WITH VARIOUS ENERGY-DEPENDENT REACTIONS.
BODE JC ET AL; EUR J CLIN INVEST 3(5) 436 (1973)

14.2 Ecological Information

14.2.1 Natural Pollution Sources

Occurs in a large number of fruits, honey and as the sole sugar in bull and human semen... /D-Fructose/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 723

15 Associated Disorders and Diseases

16 Literature

16.1 Consolidated References

16.2 NLM Curated PubMed Citations

16.3 Springer Nature References

16.4 Thieme References

16.5 Chemical Co-Occurrences in Literature

16.6 Chemical-Gene Co-Occurrences in Literature

16.7 Chemical-Disease Co-Occurrences in Literature

17 Patents

17.1 Depositor-Supplied Patent Identifiers

17.2 WIPO PATENTSCOPE

17.3 Chemical Co-Occurrences in Patents

17.4 Chemical-Disease Co-Occurrences in Patents

17.5 Chemical-Gene Co-Occurrences in Patents

18 Interactions and Pathways

18.1 Chemical-Target Interactions

18.2 Pathways

19 Biological Test Results

19.1 BioAssay Results

20 Taxonomy

Zebrafish Pathway Metabolite MetFrag Local CSV (Beta) | DOI:10.5281/zenodo.3457553
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

21 Classification

21.1 MeSH Tree

21.2 NCI Thesaurus Tree

21.3 ChEBI Ontology

21.4 WHO ATC Classification System

21.5 ChEMBL Target Tree

21.6 UN GHS Classification

21.7 NORMAN Suspect List Exchange Classification

21.8 CCSBase Classification

21.9 Consumer Product Information Database Classification

21.10 EPA TSCA and CDR Classification

21.11 LOTUS Tree

21.12 Glycan Naming and Subsumption Ontology (GNOme)

21.13 MolGenie Organic Chemistry Ontology

22 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. EPA Chemical Data Reporting (CDR)
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  4. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. Hazardous Substances Data Bank (HSDB)
  7. ILO-WHO International Chemical Safety Cards (ICSCs)
  8. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  9. EU Pesticides Database
  10. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  11. ChEBI
  12. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  13. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  14. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  15. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  16. Consumer Product Information Database (CPID)
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    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  17. Cosmetic Ingredient Review (CIR)
  18. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
  19. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    D-Fructose
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  20. DailyMed
  21. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  22. Therapeutic Target Database (TTD)
  23. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Fructose
  24. Natural Product Activity and Species Source (NPASS)
  25. Japan Chemical Substance Dictionary (Nikkaji)
  26. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  27. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  28. Metabolomics Workbench
  29. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  30. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  31. NIPH Clinical Trials Search of Japan
  32. NLM RxNorm Terminology
    LICENSE
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  33. Rhea - Annotated Reactions Database
    LICENSE
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    https://www.rhea-db.org/help/license-disclaimer
  34. SpectraBase
  35. Springer Nature
  36. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  37. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  38. Wikidata
  39. Wikipedia
  40. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  41. PubChem
  42. GHS Classification (UNECE)
  43. Glycan Naming and Subsumption Ontology (GNOme)
    GNOme
  44. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  45. PATENTSCOPE (WIPO)
CONTENTS