4-(3-Hydroxybutyl)phenol

Base Information

• Chemical Name: 4-(3-Hydroxybutyl)phenol
• CAS No.: 69617-84-1
• Molecular Formula: C10H14 O2
• Molecular Weight: 166.22
• Hs Code.: 2907299090
• European Community (EC) Number: 274-056-1
• NSC Number: 40514
• UNII: 12QWN45UL0
• DSSTox Substance ID: DTXSID20867834
• Nikkaji Number: J318.011E
• Wikidata: Q27155219
• Metabolomics Workbench ID: 121656
• ChEMBL ID: CHEMBL108014
• Mol file: 69617-84-1.mol

Synonyms:4-(4-hydroxyphenyl)-2-butanol;rhododendrol;rhododenol

Chemical Property of 4-(3-Hydroxybutyl)phenol

Chemical Property:

• Vapor Pressure: 0.000186mmHg at 25°C
• Melting Point: 71℃ (ethanol )
• Boiling Point: 315.4°C at 760 mmHg
• PKA: 10.12±0.15(Predicted)
• Flash Point: 153.4°C
• PSA: 40.46000
• Density: 1.096g/cm³
• LogP: 1.70560
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 117

Purity/Quality:

98%,99%, ^*data from raw suppliers

rac-Rhododendrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC1=CC=C(C=C1)O)O
• Uses: 4-(p-hydroxyphenyl)butan-2-ol is an aroma compound, useful for the treatment of hepatic diseases.

Technology Process of 4-(3-Hydroxybutyl)phenol

There total 41 articles about 4-(3-Hydroxybutyl)phenol 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%

4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) → rac-rhododendrol (69617-84-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 2h; Solvent; Enzymatic reaction;

DOI:10.1016/j.tetasy.2013.04.013

Reference yield: 99.0%

rac-rhododendrol (69617-84-1) → (R)-rhododendrol (59092-94-3,69617-84-1,501-96-2)

Guidance literature:

With alcohol dehydrogenase from Thermoanaerobium brockii; NADH-specific (R)-selective-ADH; YcnD-oxidoreductase; at 30 ℃; for 24h; pH=7.5; optical yield given as %ee; enantiospecific reaction; aq. buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/ja804816a

Reference yield: 98.0%

(E)-4-(4-hydroxyphenyl)-3-buten-2-one (22214-30-8) → rac-rhododendrol (69617-84-1) + 4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2)

Guidance literature:

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen; In methanol; at 0 - 30 ℃; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature; Time; Reflux; Inert atmosphere;

DOI:10.5560/ZNB.2014-4118

upstream raw materials:

(RS)-rhododendrol 2-O-β-D-glucopyranoside

(E)-4-(4-hydroxyphenyl)-3-buten-2-one

methanol

4-(4'-hydroxyphenyl)but-3-en-2-one

Downstream raw materials:

(+)-rhododendrol

(R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate

(R)-(+)-4-(4'-acetoxyphenyl)-2-butyl acetate

(R)-rhododendrol

Refernces

• 1、 Hamdan, Samir M.,Musa, Musa M.,Nafiu, Sodiq A.,Takahashi, Etsuko,Takahashi, Masateru. "Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus". . . Retrieved 2020/07/24.
• 2、 Kovalenko,Pratsko. "Selective hydrogenation of conjugated unsaturated ketones containing a hydroxyaryl substituent in the β-position". . p. 24 - 28. Retrieved 2017/03/16.