Rhododendrol

Base Information

• Chemical Name: Rhododendrol
• CAS No.: 501-96-2
• Deprecated CAS: 23950-20-1
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• European Community (EC) Number: 809-359-5
• UNII: 97PTR2F3Z8
• DSSTox Substance ID: DTXSID20198211
• Nikkaji Number: J12.236J
• Wikipedia: Rhododendrol
• Wikidata: Q27272029
• Metabolomics Workbench ID: 121827
• ChEMBL ID: CHEMBL1086681
• Mol file: 501-96-2.mol

Synonyms:rhododendrol;rhododenol

Chemical Property of Rhododendrol

Chemical Property:

• Melting Point: 81 °C
• Boiling Point: 315.4±17.0 °C(Predicted)
• PKA: 10.12±0.15(Predicted)
• PSA: 40.46000
• Density: 1.096±0.06 g/cm3(Predicted)
• LogP: 1.70560
• Storage Temp.: ?20°C
• 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:

99% ^*data from raw suppliers

(-)-Rhododendrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC1=CC=C(C=C1)O)O
• Isomeric SMILES: C[C@H](CCC1=CC=C(C=C1)O)O
• Uses: (-)-Rhododendrol, can be extracted from the leaves of Abies webbiana Lindl., having dendrite elongation inhibition activity in cell lines.

Technology Process of Rhododendrol

There total 29 articles about Rhododendrol 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: 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: 93.0%

(R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate (129752-69-8) → (R)-rhododendrol (59092-94-3,69617-84-1,501-96-2)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol402913m

Reference yield: 85.0%

(2R)-4-[4-(benzyloxy)phenyl]butan-2-ol (138948-80-8) → (R)-rhododendrol (59092-94-3,69617-84-1,501-96-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1080/00397910701265614

upstream raw materials:

dimethyl zinc(II)

3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde

(1R)-3-(4-hydroxyphenyl)-1-methylpropyl β-D-glucopyranoside

(2R)-4-(4-Hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside

Downstream raw materials:

1-phenyl-3-butanol

C₁₆H₂₈O₂Si

C₁₆H₂₈O₃Si

C₂₂H₄₂O₂Si₂

Refernces

• 1、 Kosjek, Birgit,Stampfer, Wolfgang,Van Deursen, Ruud,Faber, Kurt,Kroutil, Wolfgang. "Efficient production of raspberry ketone via 'green' biocatalytic oxidation". . p. 9517 - 9521. Retrieved 2003.
• 2、 Karume, Ibrahim,Takahashi, Masateru,Hamdan, Samir M.,Musa, Musa M.. "Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase". . p. 1459 - 1463. Retrieved 2016/05/02.
• 3、 Kitayama, Takashi,Isomori, Sachiko,Nakamura, Kaoru. "Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues". . p. 621 - 627. Retrieved 2013/07/19.