21311-66-0

Basic information

• Product Name: Dihydrosamidin
• Synonyms: rac Dihydro Samidin;(+/-)-3,4,5-Trihydroxy-2,2-diMethyl- 6-chroManacrylic Acid δ-Lactone 4-Acetate 3-Isovalerate;Butanoic Acid 3-Methyl-10-(acetyloxy)-9,10-dihydro-8,8-diMethyl-2-oxo- 2H,8H-benzo[1,2-b:3,4-b']dipyran-9-yl Ester
• CAS NO: 21311-66-0
• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.41106
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 21311-66-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• CAS DataBase Reference: Dihydrosamidin(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrosamidin(21311-66-0)
• EPA Substance Registry System: Dihydrosamidin(21311-66-0)

Safety Data

• Hazardous Substances Data: 21311-66-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dihydrosamidin is used as a vasodilatory agent for its ability to relax blood vessels, improving blood flow and reducing blood pressure. This makes it a valuable compound for the development of treatments for cardiovascular diseases and conditions related to poor blood circulation.
Used in Synthesis of Compounds:
Dihydrosamidin is also utilized as a key component in the synthesis of various compounds, such as (+/-)-Praeruptorin A. This application highlights its importance in the development of new drugs and therapeutic agents with potential benefits for human health.

Upstream product

• 503-74-2 3-methylbutyric acid 
• 4955-21-9 (+/-)-cis-4'-acetylkhellactone 
• 523-59-1 seseline 
• 518-76-3 (±)-cis-khellactone 
• 4955-21-9 (+/-)-trans-4'-acetylkhellactone 
• 108-12-3 isopentanoyl chloride 

Downstream Products

• 76237-63-3 3-Methyl-butyric acid 5-hydroxy-2,2-dimethyl-6-((E)-3-oxo-3-piperidin-1-yl-propenyl)-4-piperidin-1-yl-chroman-3-yl ester 
• 76237-74-6 Benzoic acid 5-hydroxy-2,2-dimethyl-4-morpholin-4-yl-6-((E)-3-morpholin-4-yl-3-oxo-propenyl)-chroman-3-yl ester 
• 76237-64-4 Acetic acid 5-hydroxy-2,2-dimethyl-6-((E)-3-oxo-3-piperidin-1-yl-propenyl)-4-piperidin-1-yl-chroman-3-yl ester 
• 76237-60-0 3'-benzoyloxy-4'-piperidino-3,',4'-dihydroseselin 

Relevant articles and documents

The antagonistic effects of khellactones on platelet-activating factor, histamine, and leukotriene D4

Khellactones of Peucedanum praeruptorum Duun., including praeruptorins A (= Pd-Ia, 2) and B (= Pd-II, 11), had an antagonistic effect specifically on platelet aggregation induced by platelet activating factor (PAF) among various aggregating agents examined, and represent a new class of PAF antagonists. We examined the effects of twenty compounds on PAF-induced platelet aggregation and on histamine- and leukotriene D4 (LTD4)-induced contractions in isolated guinea pig ileum. Compounds 2, (±)-cis-3',4'-diacetylkhellactone (3), (±)-cis-4'-acetyl-3'-crotonoylkhellactone (5), (±)-cis-4'-acetyl-3'-tetrolylkhellactone (6), (±)-cis-4'-acetyl-3'-tigloylkhellactone (7), (±)-cis-4'-acetyl-3'-(2''-methylbutyryl)khellactone (8), (±)-cis-3',4'-ditigloylkhellactone (10), and 11 all strongly inhibited PAF-induced platelet aggregation. (±)-cis-4'-Acetyl-3'-(2''-methyl-2''-dodecenoyl)khellactone (9), (±)-cis-4'-ethyl-3'-tigloylkhellactone (13), (±)-cis-4'-ethyl-3'-[N-(2''-triethylammonio)ethylcarbamoyl]khellacton e iodide (16), (±)-trans-3',4'-diacetylkhellactone (18), (±)-trans-4'-acetyl-3'-crotonoylkhellactone (19), (±)-trans-4'acetyl-3'-valerylkhellactone (20), (±)-trans-4'-acetyl-3'-isovalerylkhellactone (21), and (±)-trans-4'-acetyl-3'-tigloylkhellactone (22) were weakly inhibitory. Most of the compounds exhibited noncompetitive antagonist actions on histamine- and LTD4-induced contractions. The potencies of the antagonistic effects on histamine action were in the order 7 = 22 ≥ 2 = 8 = 10 > 6 = 11 = 13 ≥ 5 > 19 = 9 and those on LTD4 action were in the order 6 = 22 = 2 > 10 = 8 > 7 = 9 = 11 ≥ 13. Thus, compounds with potent PAF-antagonistic activities have the following features: cis isomers of khellactone at the C-3' and C-4' positions are more favorable than trans isomers, and the acyl moiety at the C-3' position of khellactone must be of an appropriate molecular size. In the case of histamine- and LTD4-antagonistic activities, both isomers show similar effects and acyl moieties of appropriate size are required at the C-3' and C-4' positions. These results are of interest in regard to the medicinal uses of Peucedanum species as a herbal drug.

SYNTHESIS OF (+/-)-PRAERUPTORIN A AND RELATED KHELLACTONE DERIVATIVES

The first synthesis of the pyranocoumarin natural product, (+/-)-praeruptorin A (= Pd-Ia), is described.A general method for the preparation of various khellactone derivatives is reported.