26577-85-5

Basic information

• Product Name: PETASIN
• Synonyms: (Z)-2-Methyl-2-butenoic acid (1R)-1,2,3,4,6,7,8,8a-octahydro-1β,8aβ-dimethyl-7α-(1-methylethenyl)-6-oxonaphthalen-2α-yl ester;(Z)-2-Methyl-2-butenoic acid [(3S)-3α-isopropenyl-4aβ,5β-dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxonaphthalene]-6α-yl ester;(2Z)-2-Methyl-2-butenoic acid (1R,2R,7S,8aR)-1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester;O-Angeloylsencathenone;Petaforce
• CAS NO: 26577-85-5
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.43452
• Mol File: 26577-85-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 66-70℃
• Boiling Point: 421.1°Cat760mmHg
• Flash Point: 181.6°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 2.68E-07mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: PETASIN(CAS DataBase Reference)
• NIST Chemistry Reference: PETASIN(26577-85-5)
• EPA Substance Registry System: PETASIN(26577-85-5)

Safety Data

• Hazardous Substances Data: 26577-85-5(Hazardous Substances Data)

Usage

Description

PETASIN, also known as an enoate ester, is a chemical compound derived from the formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphtalhen-2-ol. It is a unique molecule with potential applications in various industries due to its distinct chemical properties.

Uses

Used in Pharmaceutical Industry:
PETASIN is used as a pharmaceutical compound for its potential therapeutic effects. Its unique chemical structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs and treatments.
Used in Chemical Research:
In the field of chemical research, PETASIN serves as a valuable compound for studying the properties and reactions of enoate esters. Its structure can provide insights into the behavior of similar molecules and contribute to the advancement of chemical knowledge.
Used in Material Science:
PETASIN's unique chemical properties may also find applications in material science, where it could be used to develop new materials with specific characteristics, such as improved strength, flexibility, or chemical resistance.
Used in Environmental Applications:
Due to its chemical structure, PETASIN may have potential uses in environmental applications, such as in the development of biodegradable materials or as a component in environmental remediation processes.

InChI:InChI=1/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1

Synthetic route

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester (164414-38-4) → Isopetasin (469-26-1) + Petasin (26577-85-5)

Conditions	Yield
With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1h;	A 17% B 69%

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester (164414-38-4) → Petasin (26577-85-5)

Conditions	Yield
With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1h;	69%

Angelic acid (565-63-9) → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / toluene / 2 h / Ambient temperature 2: Et3N / toluene / 24 h / 80 °C 3: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride (137601-32-2) → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / toluene / 24 h / 80 °C 2: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

(4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one (122052-66-8) → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) HMDS, 3.) ZnCl2 2: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature 3: Et3N / toluene / 24 h / 80 °C 4: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

(3S,4aR,5R,6R)-(+)-6-hydroxy-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one (164577-44-0) → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / toluene / 24 h / 80 °C 2: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

(1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid (164414-36-2) → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: toluene / 5 h / 80 °C 2: ethanol / 15 h / Heating 3: 1.) HMDS, 3.) ZnCl2 4: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature 5: Et3N / toluene / 24 h / 80 °C 6: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

(3S,4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one (164414-37-3) → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature 2: Et3N / toluene / 24 h / 80 °C 3: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

5-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-6-oxo-cyclohexyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanoic acid phenylamide → Petasin (26577-85-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: ethanol / 15 h / Heating 2: 1.) HMDS, 3.) ZnCl2 3: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature 4: Et3N / toluene / 24 h / 80 °C 5: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C View Scheme

Upstream product

• 164414-38-4 2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester 
• 565-63-9 Angelic acid 
• 164414-37-3 (3S,4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 164414-36-2 (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid 
• 164577-44-0 (3S,4aR,5R,6R)-(+)-6-hydroxy-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 122052-66-8 (4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 137601-32-2 (2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride 

Relevant articles and documents

The total synthesis of (+)-petasin and (+)-isopetasin

Petasin 1 and isopetasin 2, anti-inflammatory and analgesic components of the butterbur (Petasites hybridus), were prepared for the first time in a short and enantioselective synthesis. The key steps were a Michael addition/alkylation (7 → 8), an enamine alkylation to give 9 and a cyclization with N-phenyliminoketenylidenetriphenylphosphorane 11 (10 → 15).