83864-78-2

Basic information

• Product Name: obovatol
• Synonyms: obovatol;5-(2-Propenyl)-3-[4-(2-propenyl)phenoxy]-1,2-benzenediol
• CAS NO: 83864-78-2
• Molecular Formula: C₁₈H₁₈O₃
• Molecular Weight: 282.33
• Mol File: 83864-78-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 413.6°C at 760 mmHg
• Flash Point: 203.9°C
• Appearance: /
• Density: 1.149g/cm³
• Vapor Pressure: 1.98E-07mmHg at 25°C
• Refractive Index: 1.601
• PKA: 9.30±0.15(Predicted)
• CAS DataBase Reference: obovatol(CAS DataBase Reference)
• NIST Chemistry Reference: obovatol(83864-78-2)
• EPA Substance Registry System: obovatol(83864-78-2)

Safety Data

• Hazardous Substances Data: 83864-78-2(Hazardous Substances Data)

Usage

General Description

Obovatol is a natural chemical compound found in the medicinal plant Magnolia species, such as Magnolia obovata and Magnolia officinalis. It has been studied for its potential health benefits, including its anti-inflammatory, anti-cancer, and neuroprotective properties. Obovatol has been shown to have antioxidant activity and may help protect cells from oxidative stress. It also has potential as a therapeutic agent for various diseases, such as cancer, cardiovascular diseases, and neurodegenerative disorders. Research on obovatol is ongoing, and its potential applications in medicine and health continue to be explored.

InChI:InChI=1/C18H18O3/c1-3-5-13-7-9-15(10-8-13)21-17-12-14(6-4-2)11-16(19)18(17)20/h3-4,7-12,19-20H,1-2,5-6H2

Synthetic route

eudesobovatol A (125196-77-2) → cryptomeridiol (60132-35-6, 92857-25-5, 108006-39-9, 122674-21-9, 143004-65-3, 4666-84-6) + obovatol (83864-78-2)

Conditions	Yield
With trifluoroacetic acid In benzene

eudesobovatol A (125196-77-2) → obovatol (83864-78-2) + eudesm-4-en-11-ol (13902-07-3, 15051-81-7, 72173-98-9, 98683-12-6, 117066-77-0, 1209-71-8)

Conditions	Yield
With trifluoroacetic acid In benzene for 10h; Ambient temperature;	A 7 mg B 2 mg

obovatol (83864-78-2) → 5-propyl-3-(4-propylphenoxy)benzene-1,2-diol (83864-79-3)

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 24h;	95%
With hydrogen; palladium on activated charcoal In acetone at 20℃;	90%
With hydrogen; palladium on activated charcoal In methanol Ambient temperature;
With ethanol; palladium on activated charcoal

obovatol (83864-78-2) + methyl iodide (74-88-4) → 3-(4-allylphenoxy)-5-allyl-2-methoxyphenol (1146930-80-4)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 5h;	90%

obovatol (83864-78-2) → 3-(4-((E)-prop-1-enyl)phenoxy)-5-((E)-prop-1-enyl)benzene-1,2-diol (1146930-90-6)

Conditions	Yield
palladium dichloride In methanol at 20℃; for 5h;	90%

formaldehyd (50-00-0) + obovatol (83864-78-2) + Ethyl nipecotate (71962-74-8) → C27H33NO5

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	89%

acetic anhydride (108-24-7) + obovatol (83864-78-2) → obovatol diacetate (83864-81-7)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 0.333333h;	82%
In pyridine Ambient temperature;

morpholine (110-91-8) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C23H27NO4

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	70%

formaldehyd (50-00-0) + 4-ethoxycarbonylpiperazine (120-43-4) + obovatol (83864-78-2) → C26H32N2O5

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	58%

formaldehyd (50-00-0) + obovatol (83864-78-2) + 3-Methylpiperidine (626-56-2, 53152-98-0) → C25H31NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	58%

formaldehyd (50-00-0) + obovatol (83864-78-2) + 4-(3-methoxyphenyl)piperazine (16015-71-7) → C30H34N2O4

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	51%

4-methylpiperidin (626-58-4) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C25H31NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	49%

1-methyl-piperazine (109-01-3) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C24H30N2O3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	45%

formaldehyd (50-00-0) + 4-phenyl-1-piperazine (92-54-6) + obovatol (83864-78-2) → C29H32N2O3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	44%

4-ethylpiperazine (5308-25-8) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C25H32N2O3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	43%

formaldehyd (50-00-0) + 1-(3-Methylphenyl)piperazine (41186-03-2) + obovatol (83864-78-2) → C30H34N2O3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	42%

formaldehyd (50-00-0) + 4-phenylpiperidine (771-99-3) + obovatol (83864-78-2) → C30H33NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	42%

isonipecotic acid methyl ester (2971-79-1) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C26H31NO5

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	40%

formaldehyd (50-00-0) + obovatol (83864-78-2) + 2-Methylpiperidin (109-05-7, 3000-79-1) → C25H31NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	39%

pyrrolidine (123-75-1) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C23H27NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	39%

formaldehyd (50-00-0) + 4-benzylpyperidine (31252-42-3) + obovatol (83864-78-2) → C31H35NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	38%

N-acetylpiperidine (13889-98-0) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C25H30N2O4

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	36%

3,5-dimethylpiperidine (35794-11-7) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C26H33NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	35%

1-(2-methoxyethyl)piperazine (13484-40-7) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C26H34N2O4

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	35%

formaldehyd (50-00-0) + obovatol (83864-78-2) + dimethyl amine (124-40-3) → C21H25NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	33%
In ethanol; water at 40 - 60℃; Mannich Aminomethylation;

formaldehyd (50-00-0) + obovatol (83864-78-2) + diethylamine (109-89-7) → C23H29NO3

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	32%

Thiomorpholin (123-90-0) + formaldehyd (50-00-0) + obovatol (83864-78-2) → C23H27NO3S

Conditions	Yield
In ethanol; water Mannich Aminomethylation; Reflux;	32%

dichloromethane (75-09-2) + obovatol (83864-78-2) → 6-Allyl-4-(4-allyl-phenoxy)-benzo[1,3]dioxole (83864-84-0)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 120℃; for 2.5h;

obovatol (83864-78-2) + 2,2-dimethoxy-propane (77-76-9) → obovatol acetonide (83864-83-9)

Conditions	Yield
In benzene for 2h; Heating;

obovatol (83864-78-2) + methyl iodide (74-88-4) → dimethylovobatol (83864-82-8)

Conditions	Yield
With potassium carbonate In acetone Heating;

Upstream product

• 125196-77-2 eudesobovatol A 

Downstream Products

• 1146930-90-6 3-(4-((E)-prop-1-enyl)phenoxy)-5-((E)-prop-1-enyl)benzene-1,2-diol 
• 1146930-80-4 3-(4-allylphenoxy)-5-allyl-2-methoxyphenol 

Relevant articles and documents

NEUROTROPHIC SESQUITERPENE-NEOLIGNANS FROM MAGNOLIA OBOVATA: STRUCTURE AND NEUROTROPHIC ACTIVITY

Novel sesquiterpene-neolignans, eudesobovatols A (1) and B (2), eudesmagnolol (3), eudeshonokiols A (4) and B (5), clovanemagnolol (6), and caryolanemagnolol (7), have been isolated from the bark of Magnolia obovata.Their structures were elucidated to be sesquiterpenes (eudesmol, 4,4,8-trimethyltricyclo2,5>dodecane-1,9-diol, and clovanediol) combined through ether bond with neolignans such as obovatol, honokiol, and magnolol on the basis of spectral data, degradation, and/or synthesis.Compounds 1, 6, and 7 were found to exhibit interesting neurotrophic activity on a neuronal cell culture system derived from fetal rat hemisphere.