Glucoheptonolactone

Base Information

• Chemical Name: Glucoheptonolactone
• CAS No.: 60046-25-5
• Molecular Formula: C₇H₁₂O₇
• Molecular Weight: 208.168
• Hs Code.: 2932209090
• European Community (EC) Number: 262-037-0
• UNII: R320ILS1YQ
• DSSTox Substance ID: DTXSID301021206
• Nikkaji Number: J2.073.459K
• Wikidata: Q27287716
• Mol file: 60046-25-5.mol

Synonyms:glucoheptonolactone;D-Glucoheptono-1,4-lactone;60046-25-5;UNII-R320ILS1YQ;R320ILS1YQ;EINECS 262-037-0;(2.xi)-D-Gluco-heptono-gamma-lactone;(4S,5S)-3,4-dihydroxy-5-[(1R,2R)-1,2,3-trihydroxypropyl]oxolan-2-one;D-gluco-Heptonic acid, .gamma.-lactone, (2.xi.)-;C7H12O7;SCHEMBL1896309;GLUCOHEPTONOLACTONE [INCI];DTXSID301021206;GLUCOHEPTONIC ACID, .GAMMA.-LACTONE;Q27287716

Chemical Property of Glucoheptonolactone

Chemical Property:

• Vapor Pressure: 9.41E-15mmHg at 25°C
• Melting Point: 152-155 °C(lit.)
• Refractive Index: 1.4455 (estimate)
• Boiling Point: 557.5°C at 760 mmHg
• PKA: 12.05±0.60(Predicted)
• Flash Point: 232.1°C
• PSA: 127.45000
• Density: 1.806g/cm³
• LogP: -3.65230
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 208.05830272
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

D-Glucoheptono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C1C(C(C(=O)O1)O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@H]1[C@H](C(C(=O)O1)O)O)O)O)O
• Uses: D-GLUCOHEPTONO-1,4-LACTONE is used in the synthesis of Howiinol A and its analogs. D-GLUCOHEPTONO-1,4-LACTONE was one of the active antitumor constituents from the root and stem bark of Goniothamus howii (Annonaceae), and it was synthesized in 9 steps from α-D-glucoheptonic γ-lactone. Twenty-six analogs were also synthesized in searching for new antitumor compounds with high potency. It is used in the synthesis of Howiinol A and its analogs. Howiinol A was one of the active antitumor constituents from the root and stem bark of Goniothamus howii (Annonaceae), and it was synthesized in 9 steps from α-D-glucoheptonic γ-lactone. Twenty-six analogs were also synthesized in searching for new antitumor compounds with high potency.

Technology Process of Glucoheptonolactone

There total 2 articles about Glucoheptonolactone 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:

D-Allose (2595-97-3) + sodium cyanide (143-33-9,25596-52-5) → D-glycero-D-altro-heptonic acid-4-lactone (89-67-8,3257-66-7,5329-44-2,10030-65-6,15397-07-6,15397-08-7,15397-09-8,22404-04-2,60046-25-5,92007-82-4) + D-glycero-D-allo-heptonic acid-4-lactone (89-67-8,3257-66-7,5329-44-2,10030-65-6,15397-07-6,15397-08-7,15397-09-8,22404-04-2,60046-25-5,92007-82-4)

Guidance literature:

With water; anschliessend Erhitzen der Reaktionsloesung unter vermindertem Druck;

DOI:10.1021/ja01628a075

Reference yield:

D-Allose (2595-97-3) + sodium cyanide (143-33-9,25596-52-5) → D-glycero-D-altro-heptonic acid-4-lactone (89-67-8,3257-66-7,5329-44-2,10030-65-6,15397-07-6,15397-08-7,15397-09-8,22404-04-2,60046-25-5,92007-82-4) + D-glycero-D-allo-heptonic acid-4-lactone (89-67-8,3257-66-7,5329-44-2,10030-65-6,15397-07-6,15397-08-7,15397-09-8,22404-04-2,60046-25-5,92007-82-4)

Guidance literature:

With water; anschliessend Erhitzen der Reaktionsloesung unter vermindertem Druck;

DOI:10.1021/ja01628a075

Reference yield:

D-glycero-D-allo-heptonic acid-4-lactone (89-67-8,3257-66-7,5329-44-2,10030-65-6,15397-07-6,15397-08-7,15397-09-8,22404-04-2,60046-25-5,92007-82-4) → L-allo-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)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous sodium hydrogenoxalate; sodium-amalgam

2: Raney nickel; water / 100 °C / 154457 Torr / Hydrogenation

3: mit Hilfe von Acetobacter suboxydans

With sodium amalgam; water; nickel; sodium hydrogen oxalate;

DOI:10.1021/ja01628a075

upstream raw materials:

D-Allose

sodium cyanide

Downstream raw materials:

D-glycero-D-allo-heptonic acid-(N'-phenyl-hydrazide)

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