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D-Mannoheptulose is a naturally occurring heptose that functions as a competitive inhibitor of glucokinases and hexokinases, which are enzymes responsible for phosphorylating D-glucose to produce glucose-6-phosphate in humans. By competing with D-glucose, D-mannoheptulose effectively blocks glucose oxidation and glucose-mediated insulin release from pancreatic islet cells. This action prevents the conversion of glucose to glucose-6-phosphate, which is essential for the activation of the carbohydrate response element binding protein. As a result, D-mannoheptulose can cause transient hyperglycemia in dogs at higher doses but not at lower doses, while also increasing postprandial energy expenditure.
Used in Pharmaceutical Industry:
D-Mannoheptulose is used as a pharmaceutical agent for normalizing insulin levels and reducing weight. Its ability to inhibit glucose phosphorylation and modulate insulin release makes it a potential candidate for the treatment of conditions related to glucose metabolism and insulin resistance.
Used in Nutritional Supplements:
D-Mannoheptulose is used as a nutritional supplement to support healthy glucose metabolism and weight management. Its presence in avocado fruit suggests that it may have a role in promoting overall health and well-being.
Used in Research Applications:
D-Mannoheptulose is used as a research tool to study the mechanisms of glucose metabolism, insulin release, and the role of glucokinases and hexokinases in various organisms. This knowledge can contribute to the development of new therapeutic strategies for managing glucose-related disorders.

3615-44-9

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3615-44-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 3615-44-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,1 and 5 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3615-44:
(6*3)+(5*6)+(4*1)+(3*5)+(2*4)+(1*4)=79
79 % 10 = 9
So 3615-44-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H14O7/c8-1-3-4(10)5(11)6(12)7(13,2-9)14-3/h3-6,8-13H,1-2H2/t3?,4-,5-,6?,7?/m1/s1

3615-44-9 Well-known Company Product Price

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  • Sigma-Aldrich

  • (73518)  D-Mannoheptulose  analytical standard

  • 3615-44-9

  • 73518-10MG

  • 3,316.95CNY

  • Detail

3615-44-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name D-Mannoheptulose

1.2 Other means of identification

Product number -
Other names D-MANNOHEPTULOSE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3615-44-9 SDS

3615-44-9Synthetic route

2-nitro-1-ethanol
625-48-9

2-nitro-1-ethanol

D-Arabinose
10323-20-3

D-Arabinose

sodium methylate
124-41-4

sodium methylate

A

D-mannoheptulose
3615-44-9

D-mannoheptulose

B

(3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one
5349-37-1

(3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one

Conditions
ConditionsYield
Behandeln des Reaktionsprodukts mit wss.Schwefelsaeure;
2-nitro-1-ethanol
625-48-9

2-nitro-1-ethanol

D-Arabinose
10323-20-3

D-Arabinose

A

D-mannoheptulose
3615-44-9

D-mannoheptulose

B

(3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one
5349-37-1

(3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one

Conditions
ConditionsYield
With methanol; sodium methylate und Behandeln des Reaktionsprodukts mit wss.Schwefelsaeure;
D-glycero-D-galactoheptose
1883-14-3, 1949-75-3, 1949-76-4, 1961-73-5, 3146-50-7, 4305-74-2, 5328-64-3, 7011-02-1, 7011-04-3, 7634-39-1, 10589-31-8, 20585-65-3, 20585-67-5, 22224-55-1, 22617-40-9, 23102-92-3, 23102-93-4, 23102-94-5, 54676-20-9, 61091-67-6, 61091-68-7, 61091-69-8, 61091-70-1, 62475-58-5, 71927-65-6, 77842-58-1, 77842-59-2, 77842-60-5, 84142-51-8, 94667-85-3

D-glycero-D-galactoheptose

D-mannoheptulose
3615-44-9

D-mannoheptulose

Conditions
ConditionsYield
With pyridine
C7H14O7

C7H14O7

D-mannoheptulose
3615-44-9

D-mannoheptulose

Conditions
ConditionsYield
With sulfuric acid; water at 60℃; for 12h;0.53 g
methanol
67-56-1

methanol

D-mannoheptulose
3615-44-9

D-mannoheptulose

methyl α-D-manno-heptulopyranoside
101629-28-1

methyl α-D-manno-heptulopyranoside

Conditions
ConditionsYield
With hydrogenchloride at 25℃; for 17h;95%
With hydrogenchloride
D-mannoheptulose
3615-44-9

D-mannoheptulose

acetone
67-64-1

acetone

1,2:3,4:6,7-tri-O-isopropylidene-D-manno-heptulofuranose
101561-45-9, 101561-46-0

1,2:3,4:6,7-tri-O-isopropylidene-D-manno-heptulofuranose

Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate at 25℃; for 24h;56%
pyridine
110-86-1

pyridine

D-mannoheptulose
3615-44-9

D-mannoheptulose

acetic anhydride
108-24-7

acetic anhydride

A

Hexa-O-acetyl-α-D-manno-[2]heptulopyranose
66904-33-4

Hexa-O-acetyl-α-D-manno-[2]heptulopyranose

B

O1,O3,O4,O5,O7-Pentaacetyl-D-manno-[2]heptulose

O1,O3,O4,O5,O7-Pentaacetyl-D-manno-[2]heptulose

L-manno-1,3,4,5,6,7-Hexahydroxy-heptan-2-on
32852-07-6

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

D-mannoheptulose
3615-44-9

D-mannoheptulose

DL-manno-1,3,4,5,6,7-Hexahydroxy-heptan-2-on
654-29-5, 3019-74-7, 3343-94-0, 3615-44-9, 4297-17-0, 5349-37-1, 7101-28-2, 13403-16-2, 15820-03-8, 22224-53-9, 22224-54-0, 29325-35-7, 31297-62-8, 32852-07-6, 79465-26-2, 98524-02-8

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

Conditions
ConditionsYield
With ethanol
D-mannoheptulose
3615-44-9

D-mannoheptulose

A

volemitol
488-38-0

volemitol

B

perseitol
527-06-0

perseitol

Conditions
ConditionsYield
With sodium amalgam
D-mannoheptulose
3615-44-9

D-mannoheptulose

2,7-anhydro-manno-2-heptulopyranose
7739-21-1

2,7-anhydro-manno-2-heptulopyranose

Conditions
ConditionsYield
With sulfuric acid
D-mannoheptulose
3615-44-9

D-mannoheptulose

acetic anhydride
108-24-7

acetic anhydride

A

Hexa-O-acetyl-α-D-manno-[2]heptulopyranose
66904-33-4

Hexa-O-acetyl-α-D-manno-[2]heptulopyranose

B

O1,O3,O4,O5,O7-Pentaacetyl-D-manno-[2]heptulose

O1,O3,O4,O5,O7-Pentaacetyl-D-manno-[2]heptulose

Conditions
ConditionsYield
With pyridine
D-mannoheptulose
3615-44-9

D-mannoheptulose

acetic anhydride
108-24-7

acetic anhydride

O1,O3,O4,O5,O7-Pentaacetyl-D-manno-[2]heptulose

O1,O3,O4,O5,O7-Pentaacetyl-D-manno-[2]heptulose

Conditions
ConditionsYield
With pyridine
D-mannoheptulose
3615-44-9

D-mannoheptulose

sulfuric acid
7664-93-9

sulfuric acid

2,7-anhydro-β-D-manno-<2>heptulopyranose

2,7-anhydro-β-D-manno-<2>heptulopyranose

D-mannoheptulose
3615-44-9

D-mannoheptulose

water
7732-18-5

water

periodic acid

periodic acid

A

formaldehyd
50-00-0

formaldehyd

B

formic acid
64-18-6

formic acid

C

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
at 20℃; zeitlicher Verlauf;
D-mannoheptulose
3615-44-9

D-mannoheptulose

sodium amalgam

sodium amalgam

A

volemitol
488-38-0

volemitol

B

d-perseitol

d-perseitol

D-mannoheptulose
3615-44-9

D-mannoheptulose

A

volemitol
488-38-0

volemitol

B

perseitol

perseitol

Conditions
ConditionsYield
With sodium amalgam
D-mannoheptulose
3615-44-9

D-mannoheptulose

methyl α-D-manno-heptuloside-7-diphenylphosphate
101561-41-5

methyl α-D-manno-heptuloside-7-diphenylphosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / HCl / 17 h / 25 °C
2: pyridine / 17 h / 25 °C / 2.2 eqv. phosphorylating reagent
View Scheme
D-mannoheptulose
3615-44-9

D-mannoheptulose

D-manno-heptulose 7-phosphate, disodium salt
101561-44-8

D-manno-heptulose 7-phosphate, disodium salt

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / HCl / 17 h / 25 °C
2: pyridine / 17 h / 25 °C / 2.2 eqv. phosphorylating reagent
3: 78 percent / hydrogen / PtO2 / methanol / 16 h / 25 °C
4: 62 percent / 0.33percent aq. H2SO4 / 0.5 h / 100 °C
View Scheme
D-mannoheptulose
3615-44-9

D-mannoheptulose

methyl α-D-manno-heptuloside 7-phosphate disodium salt
101561-43-7

methyl α-D-manno-heptuloside 7-phosphate disodium salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / HCl / 17 h / 25 °C
2: pyridine / 17 h / 25 °C / 2.2 eqv. phosphorylating reagent
3: 78 percent / hydrogen / PtO2 / methanol / 16 h / 25 °C
View Scheme
D-mannoheptulose
3615-44-9

D-mannoheptulose

methyl α-D-manno-heptuloside 1,7-bis(diphenyl phosphate)

methyl α-D-manno-heptuloside 1,7-bis(diphenyl phosphate)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / HCl / 17 h / 25 °C
2: 57 percent / pyridine / 17 h / 25 °C / 2.2 eqv. phosphorylating reagent
View Scheme

3615-44-9Relevant academic research and scientific papers

An efficient synthesis of d-mannoheptulose via oxidation of an olefinated sugar with potassium permanganate in aqueous acetone

Cheng, Jie,Fang, Zhijie,Li, Song,Zheng, Baohui,Jiang, Yuhua

experimental part, p. 2093 - 2095 (2010/03/01)

An efficient three-step synthesis of d-mannoheptulose was successfully accomplished from 2,3,4,5,6-penta-O-benzyl-d-mannose. First, an olefinated sugar was prepared from 2,3,4,5,6-penta-O-benzyl-d-mannose via a Wittig reaction. Second, the key step, a 2-h

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