67494-15-9

Basic information

• Product Name: pisiferic acid
• Synonyms: pisiferic acid
• CAS NO: 67494-15-9
• Molecular Formula: C20H28O3
• Molecular Weight: 316.438
• Mol File: 67494-15-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 195.0 to 199.0 °C
• Boiling Point: 470°Cat760mmHg
• Flash Point: 252.2°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 1.23E-09mmHg at 25°C
• Refractive Index: 1.557
• Solubility: soluble in Methanol
• PKA: 4.27±0.40(Predicted)
• CAS DataBase Reference: pisiferic acid(CAS DataBase Reference)
• NIST Chemistry Reference: pisiferic acid(67494-15-9)
• EPA Substance Registry System: pisiferic acid(67494-15-9)

Safety Data

• RTECS: SF7325030
• Hazardous Substances Data: 67494-15-9(Hazardous Substances Data)

Usage

Description

Pisiferic acid, an abietane diterpenoid, is abieta-8,11,13-trien-20-oic acid with a hydroxy group at position 12. It is a naturally occurring compound that has been isolated from the stem bark of Fraxinus sieboldiana.

Uses

Used in Pharmaceutical Industry:
Pisiferic acid is used as a pharmaceutical agent for its potential therapeutic properties. Its unique chemical structure and functional groups allow it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Cosmetic Industry:
Pisiferic acid is used as an active ingredient in cosmetics for its potential skin benefits. Its presence in natural plant sources and its unique chemical properties make it an attractive option for the formulation of skincare products.
Used in Nutraceutical Industry:
Pisiferic acid is used as a nutraceutical ingredient for its potential health-promoting effects. Its natural origin and potential biological activities make it a valuable component in dietary supplements and functional foods.

InChI:InChI=1/C20H28O3/c1-12(2)14-10-13-6-7-17-19(3,4)8-5-9-20(17,18(22)23)15(13)11-16(14)21/h10-12,17,21H,5-9H2,1-4H3,(H,22,23)/t17-,20-/m0/s1

Upstream product

• 89837-37-6 8aβ,4β-epoxydecahydro-5,5-dimethylnaphthalen-1-one 
• 86531-95-5 decahydro-4a,8,8-trimethyl-4β-(tetrahydropyran-2-yloxy)naphthalen-1α-ol 
• 86531-95-5 decahydro-4a,8,8-trimethyl-4β-(tetrahydropyran-2-yloxy)naphthalen-1β-ol 
• 89837-42-3 C₂₀H₂₈O₄ 
• 89837-43-4 C₂₀H₃₀O₃ 
• 119061-38-0 6β,20-epoxy-12-methoxyabieta-8,11,13-triene 
• 89837-44-5 6β,20-epoxyabieta-8,11,13-trien-12-ol 
• 119061-37-9 (1R,6R,7S)-5,5-Dimethyl-9-(3-oxo-butyl)-12-oxa-tricyclo[5.3.2.0^1,6]dodecan-10-one 
• 89837-34-3 decahydro-4a,8,8-trimethyl-4β-(tetrahydropyran-2-yloxy)naphthalen-1-one 
• 89837-41-2 4β,9β-epoxydecahydro-8,8-dimethylphenanthtren-3-one 
• 119061-36-8 (1R,6R,7S)-5,5-Dimethyl-10-oxo-12-oxa-tricyclo[5.3.2.0^1,6]dodecane-9-carbaldehyde 
• 89837-35-4 1β,4aβ-epoxydecahydro-8,8-dimethyl-4β-(tetrahydropyran-2-yloxy)naphthalene 
• 119061-32-4 Toluene-4-sulfonic acid (4aS,8aS)-1,1,4a-trimethyl-5-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-2-yl ester 
• 113801-88-0 (2R,3R,4aR,10aS)-2-Bromo-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-3-ol 

Downstream Products

• 24067-43-4 Ferruginol-15-saeure-ethylester 
• 99152-14-4 (+)-pisiferanol 
• 76210-23-6 pisiferin 
• 3650-09-7 carnosic acid 

Relevant articles and documents

A New Abietane Diterpene from Salvia wiedemannii Boiss

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A new total synthesis of (±)-pisiferic acid

Starting from 6-isopropyl-7-methoxy-1-tetralone 2, a new synthesis of (±)-pisiferic acid 1 has been achieved. The salient features of the present synthesis are (i) facile conversion of 2 into the cis-fused octahydrophenanthrenone 5. (ii) efficient transformation of 5 into the triester 7, and (iii) conversion of 7 into 1 involving Dieckmann cyclisation as a key reaction.

Total Synthesis of (+/-)-Pisiferic Acid

A total synthesis of (+/-)-pisiferic acid (1) has been achieved by utilising the keto ether (22) which, in turn, was prepared from the alcohol (14).Subjection of the keto ether (22) to three sequential reactions (formylation, Michael addition with methyl vinyl ketone, and intramolecular aldol condensation) provided the tricyclic ether (27) whose conversion into the methoxyabietatriene (32) was accomplished in four steps (ethoxycarbonylation, Grignard reaction with methyl-lithium, acid-catalysed dehydration, and methoxylation).Reaction of the methoxyabietatriene (32) with zinc, zinc iodide, and acetic acid produced (+/-)-pisiferol (2) which was finally converted into (+/-)-pisiferic acid (1).The ketone (34) was converted into the abietatriene (41) following exactly the same procedure adopted for the transformation of the keto ether (22) into the abietatriene (32).Hydroboration-oxidation of (41) followed by oxidation with Jones reagent and reduction with lithium aluminium hydride followed by transannular oxidation gave the abietatriene (36).