D-manno-2-Heptulose

Base Information

• Chemical Name: D-manno-2-Heptulose
• CAS No.: 3615-44-9
• Molecular Formula: C7H14O7
• Molecular Weight: 210.184
• Hs Code.: 29400090
• European Community (EC) Number: 222-795-5
• NSC Number: 226836,1217,1216
• DSSTox Substance ID: DTXSID80863079
• Wikipedia: Mannoheptulose
• Wikidata: Q47459280
• Mol file: 3615-44-9.mol

Synonyms:D-Mannoheptulose;D-manno-2-Heptulose;1,3,4,5,6,7-hexahydroxyheptan-2-one;D-Altro-2-heptulose;NSC1216;3615-44-9;(+)-Mannoheptulose;Galacto-heptulose;L-GLUCO-HEPTULOSE;NSC-226836;Hept-2-ulose;Hept-2-ulose #;GLUCOHEPTULOSE,D;SCHEMBL677788;DTXSID80863079;NSC1217;CHEBI:167607;HSNZZMHEPUFJNZ-UHFFFAOYSA-N;NSC-1216;NSC-1217;NSC226836;FT-0625543;Q47459280;47A62F9D-A0A7-4AB5-91AD-4986A524FA51

Chemical Property of D-manno-2-Heptulose

Chemical Property:

• Melting Point: 151 ºC
• Refractive Index: 1.636
• Boiling Point: 628 °C at 760 mmHg
• PKA: 11.86±0.20(Predicted)
• Flash Point: 347.6 °C
• PSA: 130.61000
• Density: 1.645 g/cm³
• LogP: -3.85890
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -3.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 210.07395278
• Heavy Atom Count: 14
• Complexity: 183

Purity/Quality:

98%, ^*data from raw suppliers

D-manno-[UL-13C7]hept-2-ulose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C(C(=O)CO)O)O)O)O)O
• 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 (Ki = 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.
• Uses: Mannoheptulose occurs naturally in avocado fruit. It is used for normalizing insulin levels and reducing weight. Mannoheptulose occurs naturally in avocado fruit.

Technology Process of D-manno-2-Heptulose

There total 18 articles about D-manno-2-Heptulose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-nitro-1-ethanol (625-48-9) + D-Arabinose (10323-20-3) → D-mannoheptulose (3615-44-9) + (3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one (5349-37-1)

Guidance literature:

With methanol; sodium methylate; und Behandeln des Reaktionsprodukts mit wss.Schwefelsaeure;

DOI:10.1021/ja01543a043

Reference yield:

C7H14O7 → D-mannoheptulose (3615-44-9)

Guidance literature:

With sulfuric acid; water; at 60 ℃; for 12h;

DOI:10.1016/j.carres.2009.06.020

Reference yield:

2-nitro-1-ethanol (625-48-9) + D-Arabinose (10323-20-3) + sodium methylate (124-41-4) → D-mannoheptulose (3615-44-9) + (3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one (5349-37-1)

Guidance literature:

Behandeln des Reaktionsprodukts mit wss.Schwefelsaeure;

DOI:10.1021/ja01543a043

upstream raw materials:

2-nitro-1-ethanol

D-Arabinose

sodium methylate

D-glycero-D-galactoheptose

Downstream raw materials:

DL-manno-1,3,4,5,6,7-Hexahydroxy-heptan-2-on

volemitol

perseitol

2,7-anhydro-manno-2-heptulopyranose

Refernces

• 1、 Cheng, Jie,Fang, Zhijie,Li, Song,Zheng, Baohui,Jiang, Yuhua. "An efficient synthesis of d-mannoheptulose via oxidation of an olefinated sugar with potassium permanganate in aqueous acetone". experimental part. p. 2093 - 2095. Retrieved 2010/03/01.