76497-23-9

Basic information

• Product Name: dl-β-costal
• CAS NO: 76497-23-9
• Molecular Weight: 218.339
• Mol File: 76497-23-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: dl-β-costal(CAS DataBase Reference)
• NIST Chemistry Reference: dl-β-costal(76497-23-9)
• EPA Substance Registry System: dl-β-costal(76497-23-9)

Safety Data

• Hazardous Substances Data: 76497-23-9(Hazardous Substances Data)

Upstream product

• 515-20-8 dl-β-costol 
• 4966-46-5 Methanesulfonic acid (2S,4aR,8aS)-4a-methyl-8-methylene-decahydro-naphthalen-2-yl ester 
• 72715-02-7 (1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol 
• 72715-06-1 4α-hydroxyeudesm-11-en-12-al 
• 88719-08-8 germacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-12-al 
• 69427-73-2 (+)-β-costol 

Downstream Products

• 3650-43-9 (+/-)-Cortysaeure 
• 515-20-8 dl-β-costol 

Relevant articles and documents

Gastric cytoprotective activity of ilicic aldehyde: Structure-activity relationships

A series of sesquiterpene compounds possessing both eudesmane and eremophilane skeletons were tested as gastric cytoprotective agents on male Wistar rats. The presence of an α,β-unsaturated aldehyde on the C-7 side chain together with a hydroxyl group at C-4 is the requirement for the observed antiulcerogenic activity. In an attempt to establish new molecular structural requirements for this gastric cytoprotective activity, a structure-activity study was performed.

Functionalization of trans-Decalin. IV. A Stereoselective Synthesis of dl-β-Costol, dl-Arctiol, and the Related Eudesmane Type Sesquiterpenes

The efficient synthetic procedures to dl-β-costol (1a), dl-arctiol (2), and the related eudesmane type sesquiterpenes are described. trans-8,8-Ethylenedioxy-4aβ-methyldecalin-2α-ol (6a), prepared from trans-1,1-ethylenedioxy-4aβ-methyl-Δ6,7-octalin by epoxydation and subsequent reduction of the epoxy ring, was converted into 1a as follows: (1) deacetalization of 6a followed with mesylation, giving 2α-methylsulfonyloxy-4aβ-methyldecalin-8-one (7b), (2) condensation of 7b with methyl sodiomalonate and subsequent Wittig reaction with methylenetriphenylphosphorane affording dimethyl (trans-4aβ-methyl-1-methylene-7β-decalinyl)malonate (9), (3) reduction of sodium salt of 9 with NaAl(OCH2CH2OMe)2H2.Oxidation of 1a with PCC gave dl-β-costal. dl-Arctiol (2), structurally related to 1a, was prepared from trans-5,5-ethylenedioxy-8aβ-methyldecalin-2-one.Introduction of two equatorial substituents, such as hydroxyl and 1-hydroxy-1-methylethyl groups at the C-2 and C-3 carbons of 2, was carried out as follows:(1) methoxycarbonylation followed by methylation of the sodium salt of keto ester with MeLi, (2) subsequent reduction with lithium in liquid NH3, giving trans-5,5-ethylenedioxy-3β-(1-hydroxy-1-methylethyl)-8aβ-methyldecalin-2α-ol (14), and (3) deacetalization of 14 followed by the reaction with methylenetriphenylphosphorane. dl-Eudesma-4(14,7(11)-dien-8-one was also prepared from 2 by oxidation with PCC followed by dehydration and subsequent isomerization of double bond.

Studies leading to the stereoselective total synthesis of dl-beta-eudesmol, dl-beta-selinene, dl-costol, and related naturally occurring sesquiterpenes.

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