(3R)-hydroxy-beta-ionone

Base Information

• Chemical Name: (3R)-hydroxy-beta-ionone
• CAS No.: 50281-38-4
• Molecular Formula: C13H20O2
• Molecular Weight: 208.301
• DSSTox Substance ID: DTXSID80456187
• Nikkaji Number: J1.230.498F,J1.643.347K
• Wikidata: Q27123998
• Metabolomics Workbench ID: 58581
• Mol file: 50281-38-4.mol

Synonyms:(3R)-hydroxy-beta-ionone;Apo-9-zeaxanthinone;50281-38-4;(E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]but-3-en-2-one;(3R)-3-Hydroxy-beta-ionone;(3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one;(R,E)-4-(4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one;3-Hydroxy-b-ionone;(?)-3-Hydroxy-beta-ionone;SCHEMBL10451761;CHEBI:53173;DTXSID80456187;Q27123998;1-(4beta-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-1-butene-3-one

Chemical Property of (3R)-hydroxy-beta-ionone

Chemical Property:

• Boiling Point: 333.0±25.0 °C(Predicted)
• PKA: 14.82±0.70(Predicted)
• PSA: 37.30000
• Density: 1.038±0.06 g/cm3(Predicted)
• LogP: 2.62900
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 208.146329876
• Heavy Atom Count: 15
• Complexity: 321

Purity/Quality:

97% ^*data from raw suppliers

(3R)-3-Hydroxy-β-ionone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)O)(C)C)C=CC(=O)C
• Isomeric SMILES: CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=O)C
• Uses: A naturally occurring apocaratenoid that is produced from (3R)-β-Cryptoxanthin (C827500) by oxidative cleavage catalyzed by the caratenoid cleavage oxygenase RdCCD1.

Technology Process of (3R)-hydroxy-beta-ionone

There total 27 articles about (3R)-hydroxy-beta-ionone 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: 100.0%

(S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one (83021-07-2) → (3R)-3-hydroxy-β-ionone (50281-38-4)

Guidance literature:

With hydrogen fluoride;

DOI:10.3987/com-99-s54

Reference yield: 100.0%

(R)-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-3-enyl 3,5-dinitrobenzoate → (3R)-3-hydroxy-β-ionone (50281-38-4)

Guidance literature:

With methanol; diethylamine; In tetrahydrofuran; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Catalytic behavior; Kinetics; Inert atmosphere;

DOI:10.1248/cpb.c17-00462

Reference yield: 99.0%

(3R)-3-Acetoxy-β-ionon (54165-55-8) → (3R)-3-hydroxy-β-ionone (50281-38-4)

Guidance literature:

With potassium hydroxide; In methanol; dichloromethane; at 0 ℃; for 2h; optical yield given as %ee;

DOI:10.1055/s-0030-1258382

upstream raw materials:

isoxazoline

C₁₉H₃₄O₂Si

C₁₁H₁₈O

C₁₁H₁₈O

Downstream raw materials:

(3R)-3-Hydroxy-β-jonon-trisylhydrazon

4-<(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>butan-2-one

(S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

C₄₇H₄₆O₁₁