501-96-2

Basic information

• Product Name: rhododendrol
• Synonyms: rhododendrol;(-)-Betuligenol;(2R)-4-(4-Hydroxyphenyl)butane-2-ol;(R)-3-(4-Hydroxyphenyl)-1-methyl-1-propanol;[R,(-)]-4-Hydroxy-α-methylbenzene-1-propanol;4-[(R)-3-Hydroxybutyl]phenol;(R)-(-)-Rhododendrol
• CAS NO: 501-96-2
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.21696
• Mol File: 501-96-2.mol

Chemical Properties

• Melting Point: 81 °C
• Boiling Point: 315.4±17.0 °C(Predicted)
• Appearance: /
• Density: 1.096±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 10.12±0.15(Predicted)
• CAS DataBase Reference: rhododendrol(CAS DataBase Reference)
• NIST Chemistry Reference: rhododendrol(501-96-2)
• EPA Substance Registry System: rhododendrol(501-96-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 501-96-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Rhododendrol is used as a bioactive compound for its dendrite elongation inhibition activity in cell lines. This property can be exploited for the development of new drugs targeting specific cellular processes, potentially leading to treatments for various diseases and conditions.
Used in Research and Development:
In the field of research and development, rhododendrol can be utilized as a key component in the study of cell line behavior and the development of novel therapeutic strategies. Its unique properties may provide valuable insights into cellular mechanisms and contribute to the advancement of medical science.
Used in Cosmetics Industry:
Given its potential bioactive properties, rhododendrol may also find applications in the cosmetics industry. It could be incorporated into skincare products for its possible anti-aging, cell regeneration, or other beneficial effects on the skin.
Used in Agricultural Industry:
Rhododendrol's bioactive properties may also be harnessed in the agricultural industry, where it could be used to develop new plant growth regulators or as a component in the production of biopesticides.

InChI:InChI=1S/C10H14O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-8,11-12H,2-3H2,1H3/t8-/m1/s1

Upstream product

• 544-97-8 dimethyl zinc(II) 
• 147974-20-7 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde 
• 65982-27-6 (1R)-3-(4-hydroxyphenyl)-1-methylpropyl β-D-glucopyranoside 
• 146609-83-8 (2R)-4-(4-Hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside 
• 39516-05-7 (R)-4-(4′-methoxyphenyl)-2-butanol 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 129752-69-8 (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate 
• 85120-75-8 (R)-(+)-4-(4'-acetoxyphenyl)-2-butyl acetate 
• 69617-84-1 rac-rhododendrol 
• 138948-80-8 (2R)-4-[4-(benzyloxy)phenyl]butan-2-ol 
• 944335-20-0 4-{2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}phenol 
• 944335-21-1 (4S)-4-[4-(benzyloxy)phenethyl]-2,2-dimethyl-1,3-dioxolane 
• 944335-22-2 (2S)-4-[4-(benzyloxy)phenyl]butane-1,2-diol 
• 944335-23-3 (2S)-4-[4-(benzyloxy)phenyl]-2-hydroxybutyl 4-methyl-1-benzenesulfonate 

Downstream Products

• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 59092-94-3 (+)-rhododendrol 
• 129752-69-8 (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate 
• 1482494-92-7 C₂₂H₄₂O₂Si₂ 
• 1482494-94-9 C₁₆H₂₈O₃Si 
• 1482494-93-8 C₁₆H₂₈O₂Si 
• 1195113-83-7 (R)-4-(3-hydroxybutyl)-4-hydroperoxy-2,5-cyclohexadien-1-one 
• 1195113-90-6 (R)-4-(3-hydroxybutyl)-4-hydroxy-2,5-cyclohexadien-1-one 
• 152339-90-7 rhododendrin pentapivalate 
• 65982-27-6 (1R)-3-(4-hydroxyphenyl)-1-methylpropyl β-D-glucopyranoside 
• 2344-70-9 1-phenyl-3-butanol 
• 66264-83-3 4-(4-methoxyphenyl)butan-2-amine 
• 152339-92-9 (R)-4-(p-pivaloyloxyphenyl)butan-2-ol 

Relevant articles and documents

STEREOCHEMISTRY OF 4-ARYL-2-BUTANOLS FROM HIMALAYAN TAXUS BACCATA

4-(4'-Hydroxyphenyl)-2R-butanol, 4-(3',4'-dihydroxyphenyl)-2R-butanol and 4-(3'-methoxy-4'-hydroxyphenyl)-2R-butanol have been isolated from the needles of Himalayan Taxus baccata.These two compounds have not previously been reported in stereospecific forms.Their stereochemistry has been determined by enzymatic reduction of their corresponding 2-butanones.Key Word Index - Taxus baccata; Taxaceae; 4-aryl-2-butanol, stereochemistry; enzymatic reduction; baker's yeast.

Efficient production of raspberry ketone via 'green' biocatalytic oxidation

For the development of a 'green' oxidation method, the transformation of 4-(p-hydroxyphenyl)butan-2-ol (rhododendrol) into 4-(p-hydroxyphenyl) butan-2-one (raspberry ketone) was used as a model reaction. Different lyophilized cells of Rhodococcus spp. have been screened for their ability to perform the desired oxidation. Rhodococcus equi IFO 3730 and R. ruber DSM 44541 were able to use acetone as a hydrogen acceptor in a hydrogen transfer-like process. The oxidation can be performed at substrate concentrations up to 500 g/L.

Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus

We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.

Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase

We developed a single-enzyme-mediated two-step approach for deracemization of secondary alcohols. A single mutant of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase enables the nonstereoselective oxidation of racemic alcohols to ketones, followed by a stereoselective reduction process. Varying the amounts of acetone and 2-propanol cosubstrates controls the stereoselectivities of the consecutive oxidation and reduction reactions, respectively. We used one enzyme to accomplish the deracemization of secondary alcohols with up to >99 % ee and >99.5 % recovery in one pot and without the need to isolate the prochiral ketone intermediate.

Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues

The achiral zingerone 1, readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp. (Meito QLM) and vinyl acetate in i-Pr2O or hexane at 35 C within 1 h gave the alcohol (S)-2 and the acetate (R)-9 with high enantioselectivity without producing acetylated by-products. Since optically active (S)-2 and (R)-9 were obtained through lipase-catalyzed transesterification, other enantiomerically pure novel compounds could all be synthesized.

Cephalosporolide B serving as a versatile synthetic precursor: Asymmetric biomimetic total syntheses of cephalosporolides C, E, F, G, and (4-OMe-)G

Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

Concise enantioselective synthesis of the ten-membered lactone cephalosporolide G and its C-3 epimer

A short and highly stereo-selective sequence for the first enantioselective total synthesis of the naturally occurring 10-membered lactone, which was obtained in only eight steps, was reported. The macrolactone ring was carried out by the use of a high-yielding pyridinium chlorochromate (PCC)-mediated oxidative cleavage of a bicyclic intermediate, generated in a domino sequence from a p-peroxyquinol. The synthesis was started with (-)-rhododendrol, which was obtained by enzymatic resolution of the racemic derivative. Phenol (R)-5 was submitted to an oxidative dearomatisation process with singlet oxygen, generated from Oxone in the presence of NaHCO3. The treatment of compound peroxyquinol with para-toluene sulfonic acid followed by Triton B gave, in one step and 49% yield, the tricyclic epoxide bicyclic derivative. A similar route was employed for the synthesis of the C-3 diastereoisomer of the natural product, which was obtained in only 7 steps and 15.2% overall yield.

Orchestration of concurrent oxidation and reduction cycles for stereoinversion and deracemisation of sec-alcohols

Black and white are opposites as are oxidation and reduction. Performing an oxidation, for example, of a sec-alcohol and a reduction of the corresponding ketone in the same vessel without separation of the reagents seems to be an impossible task. Here we show that oxidative cofactor recycling of NADP + and reductive regeneration of NADH can be performed simultaneously in the same compartment without significant interference. Regeneration cycles can be run in opposing directions beside each other enabling one-pot transformation of racemic alcohols to one enantiomer via concurrent enantioselective oxidation and asymmetric reduction employing defined alcohol dehydrogenases with opposite stereo- and cofactor-preference. Thus, by careful selection of appropriate enzymes, NADH recycling can be performed in the presence of NADP+ recycling to achieve overall, for example, deracemisation of sec-alcohols or stereoinversion representing a possible concept for a "green" equivalent to the chemical-intensive Mitsunobu inversion.

Asymmetric synthesis of (R)-(-)-rhododendrol, the aglycone of the hepatoprotective agent rhododendrin

Starting from 2,3-O-isopropylidene-D-glyceraldehyde (3) as chiral material, (R)-(-)-rhododendrol 2, the aglycone of the naturally occurring rhododendrin 1 was synthesized. Copyright Taylor & Francis Group, LLC.

Resolution of racemic rhododendrol by lipase-catalyzed enantioselective acetylation

Both (R)- and (S)-enantiomers of rhododendrol were prepared in high enantiomeric exess by lipase from Pseudomonas cepacia (Amano PS)-catalyzed acetylation of racemic 1 with vinyl acetate at room temperature. Especially, in the case of using acetonitrile as the solvent, by-products 4 and 5 were minimized.