6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol

Base Information

• Chemical Name: 6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
• CAS No.: 8050-07-5
• Molecular Formula: C7H13NO4
• Molecular Weight: 512.73
• European Community (EC) Number: 232-474-1
• DSSTox Substance ID: DTXSID50865904
• Mol file: 8050-07-5.mol

Synonyms:6-amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol;SCHEMBL352747;DTXSID50865904;BCP20370;SB47811;FT-0639443;8050-07-5

Chemical Property of 6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol

Chemical Property:

• PSA: 80.67000
• Density: 0.862-0.889
• LogP: 6.83930
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 175.08445790
• Heavy Atom Count: 12
• Complexity: 194

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): A skin irritant.
• Hazard Codes: A skin irritant.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(C(C(C1N)O)O)O)CO
• Description: Olibanum gum is yellowish to yellow-green transparent beaded solid. Soluble in ethanol, chloroform and ether; insoluble in turpentine; insoluble in water. Used in the system of varnish, chewing gum flavor, medicine, etc.

Technology Process of 6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol

There total 4 articles about 6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol 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: 96.0%

3-O-acetyl-β-boswellic acid (5968-70-7) → 3-O-acetyl-11-keto-β-boswellic acid (8050-07-5)

Guidance literature:

With tert.-butylhydroperoxide; manganese(III) triacetate dihydrate; In decane; ethyl acetate; at 50 ℃; Reagent/catalyst; Solvent; Temperature; Time; Molecular sieve; Green chemistry;

DOI:10.1007/s10600-013-0451-1

Reference yield: 91.0%

acetyl chloride (75-36-5) + 11-keto-β-boswellic acid → 3-O-acetyl-11-keto-β-boswellic acid (8050-07-5)

Guidance literature:

With pyridine; dmap; at 25 ℃; for 6h;

DOI:10.1080/14786419.2018.1564295

Reference yield:

acetic anhydride (108-24-7) + 11-keto-β-boswellic acid → 3-O-acetyl-11-keto-β-boswellic acid (8050-07-5)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1016/j.ejmech.2011.01.061

upstream raw materials:

3-O-acetyl-β-boswellic acid

beta-boswellic acid

acetic anhydride

acetyl chloride

Downstream raw materials:

3-O-acetyl-β-boswellic acid

Refernces

• 1、 Sharma, Simmi,Gupta, Shilpa,Khajuria, Vidushi,Bhagat, Asha,Ahmed, Zabeer,Shah, Bhahwal Ali. "Analogues of boswellic acids as inhibitors of pro-inflammatory cytokines TNF-α and IL-6". supporting information. p. 695 - 698. Retrieved 2016/01/09.
• 2、 Shenvi, Suvarna,Reddy, G. Chandrasekara. "Reagent optimization for allylic oxidation of 3-O-acetyl-β-boswellic acid into 3-O-acetyl-11-oxo-β-boswellic acid". . p. 1008 - 1012. Retrieved 2013/04/23.