Granaticin A

Base Information

• Chemical Name: Granaticin A
• CAS No.: 19879-06-2
• Molecular Formula: C₂₂H₂₀O₁₀
• Molecular Weight: 444.395
• UNII: 98K5Y1HV1I
• Wikidata: Q76422762

Synonyms:granaticin;granaticin A;granatomycins;litmomycin

Chemical Property of Granaticin A

Chemical Property:

• Vapor Pressure: 1.6E-23mmHg at 25°C
• Melting Point: 211-213° (dec)
• Refractive Index: 1.5376 (estimate)
• Boiling Point: 748.3°Cat760mmHg
• PKA: 6.56±0.70(Predicted)
• Flash Point: 266.8°C
• PSA: 159.82000
• Density: 1.77g/cm³
• LogP: 0.28820
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 0
• Exact Mass: 444.10564683
• Heavy Atom Count: 32
• Complexity: 958

Purity/Quality:

99% ^*data from raw suppliers

GRANATICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=C(C3C(O1)CC(=O)O3)C(=C4C(=C2O)C(=O)C5=C(C4=O)C6CC(C5(C(O6)C)O)O)O
• Isomeric SMILES: C[C@H]1C2=C([C@H]3[C@@H](O1)CC(=O)O3)C(=C4C(=C2O)C(=O)C5=C(C4=O)[C@H]6C[C@H]([C@]5([C@H](O6)C)O)O)O
• General Description: Granaticin-A is a complex polyketide-derived antibiotic and antitumor agent characterized by its unique 8,11-ethanofuro[2,3-e]naphtho[2,3-c:6,7-c']dipyran trione structure. It exhibits significant biological activity, including antimicrobial properties against Gram-positive bacteria and potential cytotoxicity against cancer cells. Granatcin-A's mechanism of action involves intercalation into DNA, inhibiting nucleic acid synthesis. Its tetrahydroxy and dimethyl substitutions contribute to its stability and bioactivity. Granaticin-A and its derivatives have been studied for their therapeutic potential, though further research is needed to fully elucidate their pharmacological applications.

Technology Process of Granaticin A

There total 4 articles about Granaticin A 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:

(3aR*,5R*,8R*,9S*,11S*,13bR*,15S*)-8,9-dihydroxy-6,7,12,13-tetramethoxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-11,8-(epoxymethano)-2H-furo<3,2-b>anthra<2,3-d>pyran-2-one (108168-52-1,108266-36-0,108266-37-1,108266-38-2,124094-68-4) → (+/-)-granaticin (19879-06-2,108267-38-5,108267-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / camphorsulfonic acid / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) 18percent aq. ceric ammonium nitrate, 2.) AlCl₃, Et₂S / 1.) MeCN, 25 deg C, 2.) CH₂Cl₂, 0 deg C, 10 min; r.t., 50 min

With aluminium trichloride; ammonium cerium(IV) nitrate; diethyl sulphide; camphor-10-sulfonic acid; In tetrahydrofuran;

DOI:10.1021/ja00245a035

Reference yield:

C26H30O10 (108168-52-1,108266-36-0,108266-37-1,108266-38-2,124094-68-4) → (3aR*,5R*,8S*,9R*,11R*,13bR*,15R*)-7,8,9,12-tetrahydroxy-5,15-dimethyl-6,13-dioxo-3,3a,5,6,8,9,10,11,13,13a-decahydro-11,8-(epoxymethano)-2H-furo<2,3-b>anthra<2,3-d>pyran-2-one (19879-06-2,108267-38-5,108267-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: camphorsulfonic acid / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) 18percent aq. ceric ammonium nitrate, 2.) AlCl₃, Et₂S / 1.) MeCN, 25 deg C, 2.) CH₂Cl₂, 0 deg C, 10 min; r.t., 50 min

With aluminium trichloride; ammonium cerium(IV) nitrate; diethyl sulphide; camphor-10-sulfonic acid; In tetrahydrofuran;

DOI:10.1021/ja00245a035

Reference yield:

C29H34O10 (108168-53-2,108266-39-3) → (3aR*,5R*,8S*,9R*,11R*,13bR*,15R*)-7,8,9,12-tetrahydroxy-5,15-dimethyl-6,13-dioxo-3,3a,5,6,8,9,10,11,13,13a-decahydro-11,8-(epoxymethano)-2H-furo<2,3-b>anthra<2,3-d>pyran-2-one (19879-06-2,108267-38-5,108267-39-6)

Guidance literature:

With aluminium trichloride; ammonium cerium(IV) nitrate; diethyl sulphide; Yield given. Multistep reaction; 1.) MeCN, 25 deg C, 2.) CH₂Cl₂, 0 deg C, 10 min; r.t., 50 min;

DOI:10.1021/ja00245a035

upstream raw materials:

C₂₉H₃₄O₁₀

(3aR*,5R*,8R*,9S*,11S*,13bR*,15S*)-8,9-dihydroxy-6,7,12,13-tetramethoxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-11,8-(epoxymethano)-2H-furo<3,2-b>anthra<2,3-d>pyran-2-one

C₂₉H₃₄O₁₀

C₂₆H₃₀O₁₀

Refernces

Pyranonaphthoquinone Antibiotics. Part 1. Syntheses of 9-Demethoxyeleutherins and 9-Deoxynanaomycin A Methyl Ester.

10.1039/P19810001191

The research focuses on the synthesis of 9-demethoxyeleutherins and 9-deoxynanaomycin A methyl ester, which are pyranonaphthoquinone antibiotics known for their antimicrobial properties. The study aims to develop new synthetic routes to these complex molecules, potentially leading to the total synthesis of even more complex compounds like griseusin A and granaticin. The synthesis processes involve the use of indan-1-one derivatives as precursors, employing various chemical reactions such as Lemieux-Johnson oxidation, lithium aluminium hydride reduction, and Diels-Alder reactions. Key chemicals used in the process include indanone derivatives, methanol, acetonitrile, cerium(IV) ammonium nitrate, and methoxycarbonylmethylene-triphenylphosphorane.

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