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Beta-D-Fructopyranose

HCID 24310
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
7660-25-5
Standard SMILES
OC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O
InChIKey
LKDRXBCSQODPBY-ARQDHWQXSA-N
Molecular formula
C6H12O6
Average molar mass
180.16 g/mol
Monoisotopic mass
180.0633881

Overview

Beta-D-fructopyranose is a D-fructopyranose in which the anomeric centre has beta-configuration. It is an enantiomer of a beta-L-fructopyranose.

Names & identifiers

Preferred name
Beta-D-Fructopyranose
IUPAC
(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
English name
beta-D-Fructopyranose
Molecular formula
C6H12O6
Molecular weight
180.16

Names & synonyms

beta-D-Fructopyranose7660-25-5(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrolCHEBI:41005DTXSID0023082RefChem:937010GlyTouCan:G31484IMDTXCID503082G31484IM(2R,3S,4R,5R)-2-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol3oaybeta-fructopyranose
Show more names
Fructopyranoseβ-D-FructopyranoseS(-)-FRUCTOSEFrutabsLevungenLaevoralFructosterilFRUCTOSE HPLCFructose powderFructose,HPLC≥96%
MFCD00065409BETA-D-FRUCTOPYRANOSE [HSDB]F0060D85171Fructopyranose, beta-D-BDF|A-D-fructopyranoseHSDB 526

Database identifiers

CAS
7660-25-5
PubChem CID
24310
DTXSID
DTXSID0023082
ChEBI

Properties

Computed structural properties

XLogP
-2.8
Topological polar surface area
110 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
12
Formal charge
0
Complexity
162

Experimental & physicochemical properties

OdorODORLESS
TasteSWEET
Color/Form · 3 items

CLEAR COLORLESS LIQUID IN WATER

COLORLESS CRYSTALS OR AS A WHITE, CRYSTALLINE OR GRANULAR POWDER

White crystals

Other Experimental Properties · 2 items

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/

MP: 103 °C (dec); density: 1.60 @ 20 °C/4 °C /beta-levulose/

Physicochemical properties

Melting point
103 °C · 103°C
Boiling point
232.96 °C · 232.96°C (rough estimate)
Density
1.6 · 1.6000

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory Information · 2 items

Chemical: .beta.-D-Fructopyranose

.beta.-D-Fructopyranose: 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.

Other Safety InformationIMAP assessments - .beta.-D-Fructopyranose: Human health tier I assessment

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Interactions · 2 items

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.

REDUCTION IN MUTAGENICITY OF CIGARETTE SMOKE BY INTERACTION OF SMOKE CONDENSATES WITH ADDED FRUCTOSE.

Natural Pollution SourcesOccurs in a large number of fruits, honey and as the sole sugar in bull and human semen... /D-Fructose/
Human Toxicity Excerpts · 2 items

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).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

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.

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.

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.

Absorption, Distribution and Excretion · 2 items

TWICE THE CONCN OF FRUCTOSE CAN BE INFUSED AT THE SAME RATE AS DEXTROSE WITH BETTER RETENTION AND LESS DISTURBANCE OF FLUID BALANCE.

...ADVANTAGES OF FRUCTOSE IS ITS RAPID REMOVAL FROM EXTRACELLULAR SPACE, & THEREFORE, URINARY EXCRETION IS MINIMIZED.

Uses & manufacturing

Uses · 5 items

MEDICATION (VET)

MEDICATION

To prevent sandiness in ice cream /D-Fructose/

Therap cat: Fluid and nutrient replenisher, and ferric form as hematinic. /D-Fructose/

For more Uses (Complete) data for FRUCTOSE (9 total), please visit the HSDB record page.

U.S. Imports(1985) 1.95X10+9 g /levulose/
U.S. Production · 4 items

(1976) 9X10+11 G (HIGH FRUCTOSE CORN SYRUP-EST

(1980) 2.66X10+12 g /total indust distribution of high-fructose corn syrup/

(1980) 3.20X10+9 g /consumption of crystalline fructose/

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/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEBI:41005
UNII
R73GS1TJE0
Nikkaji
J53.982A
refractive index
1.617 · 1.6170 (estimate)
storage temp.
2 · Storage temp. 2-8°C
pka
11.52 · 11.52±0.70(Predicted)
form
Solid
color
White to off-white
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-/s3
InChIKey
LKDRXBCSQODPBY-ZSYVZJKANA-N
SMILES
C([C@]1(OC[C@@H](O)[C@@H](O)[C@@H]1O)O)O |&1:1,4,6,8,r|
CAS DataBase Reference
7660 · 7660-25-5
FDA UNII
73 GS1TJE0 · R73GS1TJE0
NIST Chemistry Reference
Fructose(7660-25-5)
CAS Number Unlabeled
57 · 57-48-7
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Hazardous Substances Data
7660 · 7660-25-5(Hazardous Substances Data)

IV INFUSION OF FRUCTOSE DEPLETED HEPATIC ATP & TOTAL ADENOSINE PHOSPHATES IN HUMANS, THEREBY INTERFERING WITH VARIOUS ENERGY-DEPENDENT REACTIONS.

Non-Human Toxicity ExcerptsIV INFUSION OF D-FRUCTOSE DEPLETED HEPATIC ATP & TOTAL ADENOSINE PHOSPHATES IN RATS, THEREBY INTERFERING WITH VARIOUS ENERGY-DEPENDENT REACTIONS.

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338
Hazardous Substances Data
7660-25-5(Hazardous Substances Data)
Methods of Manufacturing · 5 items

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)

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/

Hydrolysis of inulin; hydrolysis of beet sugar followed by lime separation; from cornstarch by enzymic or microbial action.

Hydrolysis of sucrose produces a mixture of glucose and fructose, from which fructose can be separated by chromatography. /D-Fructose/

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/

Formulations/Preparations · 5 items

FRUCTOSE INJECTION, NF, IS STERILE SOLN OF FRUCTOSE IN WATER...10% SOLN, PH 3.0-6.0.

DOSAGE FORMS- INJECTION NF: 100 G/1000 ML; FRUCTOSE & SODIUM CHLORIDE INJECTION NF: 100 G (FRUCTOSE) & 9 G (SODIUM CHLORIDE)/1000 ML.

High-fructose corn syrups ... contain 42, 55 or 90% fructose on a dry weight basis

Crystalline fructose is essentially pure

For more Formulations/Preparations (Complete) data for FRUCTOSE (6 total), please visit the HSDB record page.

General Manufacturing Information · 3 items

HOMOGENEITY DETERMINED BY PAPER...& GAS-LIQUID CHROMOTOGRAPHY SYSTEMS...

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/

...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.

Applications

UsesFructose is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose.

Upstream & downstream products

Downstream products

PALATINOSESpinosyn ALactuloseD(-)-FructoseSpinosad D1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
河北创之源生物科技有限公司13012111162 · [email protected]
陕西晨明生物科技有限公司15529026321 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017-8007 17602929471 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
武汉卡诺斯科技有限公司027-83238443 15327105076 · [email protected]
成都川研医工生物科技有限公司18280298385;18280298385 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
杭州璟皓生物科技有限公司(原河南辛迪加生物)17513242016 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
贵州迪大科技有限责任公司0851-8475-2296 18096062265 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
郑州萃智医药科技有限公司19943855286 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
康迪斯化工(湖北)有限公司13343438265 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
山东萍聚生物科技有限公司18613662662; 18613662662 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海西格生物科技有限公司021-57810052 18930344717 · [email protected]
蚌埠丰原涂山制药有限公司[email protected]

Additional notes

DefinitionChEBI: Beta-D-fructopyranose is a D-fructopyranose in which the anomeric centre has beta-configuration. It is an enantiomer of a beta-L-fructopyranose.