D-MANNOHEPTULOSE Chemical Properties

Melting point:

148-150°C

alpha 

D20 +29° (c = 2 in H2O)

Boiling point:

628.0±55.0 °C(Predicted)

Density 

1.645±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Methanol (Slightly), Water (Slightly)

pka

11.86±0.20(Predicted)

form 

Solid

color 

White to Off-White

optical activity

+29

Merck 

13,4686

BRN 

1726433

EPA Substance Registry System

D-manno-2-Heptulose (3615-44-9)

Safety Information

Safety Statements 

24/25

WGK Germany 

2

HS Code 

29400090

D-MANNOHEPTULOSE Usage And Synthesis

Description

D-Glucose is phosphorylated by glucokinase and three tissue-specific hexokinases to produce glucose-6-phosphate in humans. D-Mannoheptulose is a heptose that inhibits glucokinases and hexokinases from diverse organisms through competition with D-glucose (K_i = 0.25 mM). It blocks glucose oxidation and glucose-mediated insulin release from pancreatic islet cells. D-Mannoheptulose prevents the conversion of glucose to glucose-6-phosphate that can mediate the activation of the carbohydrate response element binding protein. By blocking glucose phosphorylation, D-mannoheptulose causes transient hyperglycemia in dogs when given at 1 g/kg but not at 8 mg/kg, although postprandial energy expenditure is increased at the lower dose.

Chemical Properties

White Solid

Uses

Mannoheptulose occurs naturally in avocado fruit. It is used for normalizing insulin levels and reducing weight.

Definition

ChEBI: D-keto-manno-heptulose is the open chain form of D-manno-heptulose.

References

[1] H G COORE  P J R. Inhibition of glucose phosphorylation by mannoheptulose.[J]. Biochemical Journal, 1964, 91 1: 56-59. DOI: 10.1042/bj0910056
[2] S J ASHCROFT  P J R. Enzymes of glucose metabolism in normal mouse pancreatic islets.[J]. Biochemical Journal, 1970, 119 1: 5-15. DOI: 10.1042/bj1190005
[3] N DAI. Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence.[J]. Plant Cell, 1999, 11 7: 1253-1266. DOI: 10.1105/tpc.11.7.1253
[4] S J ASHCROFT  P J R  L C Weerasinghe. Interrelationship of islet metabolism, adenosine triphosphate content and insulin release.[J]. Biochemical Journal, 1973, 132 2: 223-231. DOI: 10.1042/bj1320223
[5] DANIEL JOHNSON. Glucose-dependent modulation of insulin secretion and intracellular calcium ions by GKA50, a glucokinase activator.[J]. Diabetes, 2007, 56 6: 1694-1702. DOI: 10.2337/db07-0026
[6] MING V. LI . Glucose-6-phosphate mediates activation of the carbohydrate responsive binding protein (ChREBP)[J]. Biochemical and biophysical research communications, 2010, 395 3: Pages 395-400. DOI: 10.1016/j.bbrc.2010.04.028
[7] LESLIE L MCKNIGHT. Mannoheptulose has differential effects on fasting and postprandial energy expenditure and respiratory quotient in adult Beagle dogs fed diets of different macronutrient contents.[J]. Journal of Nutritional Science, 2014, 3: e17. DOI: 10.1017/jns.2014.17

D-MANNOHEPTULOSE(3615-44-9)Related Product Information

• 3-Heptanone
• D-MANNOHEPTOSE
• Mannatide
• manninotriose
• D-Mannose
• Mannitol
• L(+)-Rhamnose monohydrate
• D-Mannitol
• D-LYXOSE
• D-MANNOHEPTULOSE
• 1,2,3-HEPTANETRIOL
• 2,2'-Oxydipropanol
• (3R,5R)-(-)-3,5-HEPTANEDIOL
• D-MANNO-[1-13C]HEPT-2-ULOSE
• 1-5-ANHYDRO-D-MANNITOL CRYSTALLINE
• 3-Deoxy-D-arabinose
• Rhamnose
• mannoheptulose hexaacetate