Hydroxycodeinone

Base Information

• Chemical Name: Hydroxycodeinone
• CAS No.: 508-54-3
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• Hs Code.: 2939190000
• European Community (EC) Number: 208-085-8
• UNII: 91138F771G
• DSSTox Substance ID: DTXSID801316557
• Nikkaji Number: J6.239A
• Wikidata: Q27271360
• Mol file: 508-54-3.mol

Synonyms:14-hydroxycodeinone;hydroxycodeinone;hydroxycodeinone, (5beta,9alpha,13alpha,14alpha)-isomer

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Chemical Property of Hydroxycodeinone

Chemical Property:

• Melting Point: 275°C (rough estimate)
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 512.2°Cat760mmHg
• PKA: 11.91±0.20(Predicted)
• Flash Point: 263.6°C
• PSA: 59.00000
• Density: 1.43g/cm³
• LogP: 1.35280
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 592

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C(=O)C=CC2(C1CC5=C3C(=C(C=C5)OC)O4)O
• Isomeric SMILES: CN1CC[C@]23[C@@H]4C(=O)C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O
• Uses: An intermediate in the preparation of Oxycodone and other alkaloid based opiate antagonists.

Technology Process of Hydroxycodeinone

There total 40 articles about Hydroxycodeinone 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: 96.5%

thebaine (115-37-7) → 14-hydroxycodeinone (508-54-3)

Guidance literature:

With formic acid; dihydrogen peroxide; In water; at 25 - 30 ℃; for 5h; Temperature; Solvent;

Reference yield: 86.0%

thebaine (115-37-7) → 8α-hydroxyoxycodone (865844-01-5) + Oxycodone (76-42-6) + 14-hydroxycodeinone (508-54-3)

Guidance literature:

thebaine; With peracetic acid; acetic acid; In water; at -5 - 20 ℃; for 1.5 - 2h;

palladium dihydroxide; In water; at 15 - 20 ℃; for 2h;

With hydrogen; In water; butan-1-ol; at 20 - 25 ℃; for 3h; under 2585.81 Torr; Product distribution / selectivity;

Reference yield: 82.0%

6-benzyloxy-4,5α-epoxy-3-methoxy-17-methylmorfina-6,8(14)-diene (36127-27-2) → 14-hydroxycodeinone (508-54-3)

Guidance literature:

6-benzyloxy-4,5α-epoxy-3-methoxy-17-methylmorfina-6,8(14)-diene; With dihydrogen peroxide; oxalic acid; acetic acid; In water; at 20 ℃;

With sodium hydroxide; In water; at 2 ℃; pH=9.2; Product distribution / selectivity;

upstream raw materials:

8β,14-dihydroxy-7,8-dihydrocodeinone

thebaine

codeine

4,5α-epoxy-3-methoxy-17-methyl-6-pyrrolidin-1-yl-morphina-6,8(14)-diene

Downstream raw materials:

14-hydroxycodeine

14-Butyryloxycodeinon

14-Valeryloxy-kodeinon

14-Propionyloxycodeinon

Refernces

• 1、 Leland, David L.,Polazzi, Joseph O.,Kotick, Michael P.. "Preparation of 8-Alkyl-14-hydroxydihydrocodeinones". . p. 4012 - 4014. Retrieved 1981.
• 2、 Sargent,Weiss. "-". . p. 987,988. Retrieved 1960.
• 3、 Iijima,Rice,Brossi. "The oxidation of thebaine with m-chloroperbenzoic acid. Studies in the (+) morphinan series. III". . p. 2135 - 2137. Retrieved 1977.
• 4、 Zhang, Qibo,Rich, Joseph O.,Cotterill, Ian C.,Pantaleone, David P.,Michels, Peter C.. "14-Hydroxylation of opiates: Catalytic direct autoxidation of codeinone to 14-hydroxycodeinone". . p. 7286 - 7287. Retrieved 2005.
• 5、 -. "Method for preparing oxycodone hydrochloride impurity B". Paragraph 0029-0032. . Retrieved 2021/10/13.
• 6、 Cantillo, David,Glotz, Gabriel,Kappe, C. Oliver. "Electrochemical N-Demethylation of 14-Hydroxy Morphinans: Sustainable Access to Opioid Antagonists". supporting information. p. 6891 - 6896. Retrieved 2020/09/15.