24144-61-4

Basic information

• Product Name: 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one
• Synonyms: (+)-cis-Khellactone;[9R,10R,(+)]-9,10-Dihydro-9,10-dihydroxy-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one;8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one
• CAS NO: 24144-61-4
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.25796
• Mol File: 24144-61-4.mol
• Article Data: 33

Chemical Properties

• Melting Point: 171.0-173.5℃
• Boiling Point: 424.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.399±0.06 g/cm3(Predicted)
• Solubility: Ethyl Acetate, THF
• PKA: 13.19±0.60(Predicted)
• CAS DataBase Reference: 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one(24144-61-4)
• EPA Substance Registry System: 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one(24144-61-4)

Safety Data

• Hazardous Substances Data: 24144-61-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one serves as a valuable building block for the synthesis of more complex molecules. Its functional groups can be further modified to create a wide range of chemical products.
Used in Research and Development:
Due to its unique structure and properties, 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one is used in research and development for studying its potential applications and understanding its chemical behavior. This can lead to the discovery of new compounds and applications in various industries.
Used in Drug Delivery Systems:
Similar to gallotannin, 8,8-Dimethyl-9α,10α-dihydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one can be employed in the development of novel drug delivery systems. Its chemical properties may allow for improved delivery, bioavailability, and therapeutic outcomes when used as a carrier for other pharmaceutical compounds.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, the compound's structure suggests that it may have potential applications in anticancer research. Further investigation into its biological activity could reveal its effectiveness as an anticancer agent or in combination with other chemotherapeutic drugs.

Upstream product

• 477-33-8 (+)-samidin 
• 523-59-1 seseline 
• 35858-46-9 hyuganin C 
• 113500-35-9 isoepoxypteryxin 
• 108-46-3 recorcinol 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 4955-20-8 8,8-dimethyl-pyrano[2,3-f]chromene-2,9,10-trione 
• 109185-82-2 1a,9c-dihydro-2,2-dimethyl-2H,8H-oxireno[c]pyrano[2,3-f][1]benzopyran-8-one 
• 477-32-7 (-)-visnadin 
• 809271-86-1 hyuganin E 
• 77331-76-1 hyuganin D 
• 53023-17-9 suksdorfin 
• 84458-88-8 campestrinol 
• 73069-28-0 (+)-cis-(3'S,4'S)-3',4'-diangeloylkhellactone 

Downstream Products

• 15575-57-2 3,4-disenecioyloxy-3,4-dihydroseselin 
• 23733-92-8 trans-4'-O-methylkhellactone 
• 54712-23-1 (-)-cis-(3'S,4'S)-khellactone 
• 518-76-3 (+)-cis-khellactone 
• 152615-14-0 qianhucomarin B 
• 4955-21-9 (+/-)-cis-4'-acetylkhellactone 
• 14017-71-1 (+/-)-cis-4'-acetyl-3'-tigloylkhellactone 
• 14017-71-1 (+/-)-4'-O-acetyl-3'-O-angeloyl-cis-khellactone 
• 4992-73-8 (+/-)-dihydrosamidine 
• 72463-78-6 cis-3'-senecioylkhellactone 
• 4970-26-7 (+/-)-3',4'-ditigloylkhellactone 
• 103162-76-1 (+/-)-9r,10t-bis-benzoyloxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one 
• 19380-05-3 (+)-lomatin 

Relevant articles and documents

Chromones and coumarins from Saposhnikovia divaricata (Turcz.) Schischk. Growing in Buryatia and Mongolia and their cytotoxicity

Ethnopharmacological relevance: Saposhnikovia divaricata (family Apiaceae) a traditional medicinal plant distributed in many provinces of China, is well known for the pharmaceutical value and has been used for rheumatic arthritis, and anxiety in children. Antiviral, antioxidant and antiproliferative activities were also mentioned. The application of this plant are recorded in the Chinese Medicine (CM) classical text the Shen Nong's Materia Medica (Shen Nong Ben Cao Jing). In this monograph S. divaricata (syn Radix Ledebouriella divaricata) is graded as a premium-grade herb, with their broad-spectrum of therapeutic applications for the treatment of cough, common cold, arthralgia, as well as in rheumatic disorders. Aim of the study: To isolate and identify chemical constituents (chromones and coumarins) from S. divaricata, collected in Buryatia and Mongolia and to study their in vitro anticancer activity against MEL-8, U-937, DU-145, MDA-MB-231 and ВТ-474 cell lines. Materials and methods: An 40% aqueous ethanol extract of the roots of S. divaricata was prepared and further successively fractionated by extraction with petroleum ether, diethyl ether, tert-butyl methyl ether and ethyl acetate. The obtained extracts were subjected to a series of chromatographic separations on silica gel for isolation of individual compounds. Isolated compounds were tested for their cytotoxicity with respect to model cancer cell lines using the conventional MTT assays. Results: Total of 15 individual compounds: coumarins scopoletin 2, bergapten 3, isoimperatorin 4, marmesin 5, (+)-decursinol 9, (?)-praeruptorin B 10, oxypeucedanin hydrate 11, chromones: hamaudol 6, cimifugin 7, 5-О-methylvisamminol 8, chromone glycosides: prim-O-glucosylcimifugin 12, sec-O-glucosylhamaudol 13, 4′-O-β-D-glucopyranosyl-5-О-methylvisamminol 14, 4′-O-β-D-glucopyranosylvisamminol (15) and also polyyne compound panaxinol 1 were isolated and characterized. The structure of dihydropyranocoumarin 10 was confirmed by X-ray diffraction analyses. HPLC-UV method was used for determination of the content of most abundant chromones 7, 12 and 14 in the roots of S. divaricata, collected in Mongolia. Compounds 3–11 and 13, 14 were evaluated for their cytotoxicity with respect to model cancer cell lines. All the compounds were non-toxic in the hemolysis test. Conclusion: This report about the phytochemical profiles of S. divaricata growing in Mongolia and Buryatia led to the identification of 14 compounds including coumarins and chromones. The available coumarins and chromones may serve as new leads for the discovery of anticancer drugs.

ISOSAMIDIN ANALOG AND SAMIDIN ANALOG PRODUCTION METHOD

PROBLEM TO BE SOLVED: To provide a simple method of industrial-scale production of an isosamidin analog or samidin analog. SOLUTION: In the production method, a compound represented by the formula (1) in the figure is 1) senecioylated and 2) acetylated. [X is O or the like; R1 are each independently a C1-3 alkyl group or the like; R2 is H or the like; R3 are each a C1-3 alkyl group; m is an integer from 0 to 2; n is 1 or 2; and the symbol * represents an asymmetric center.] SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Antidiabetic effect, antioxidant activity, and toxicity of 3′,4′-Di-O-acetyl-cis-khellactone in Streptozotocin-induced diabetic rats

Pyranocoumarins are compounds with an important pharmacological profile, such as anti-inflammatory, antioxidant, cytotoxic, antiviral, antibacterial, and hypoglycemic effects. These molecules have a widespread presence as secondary metabolites in medicinal plants used to treat Diabetes Mellitus (DM). The aim of this work was to evaluate antidiabetic activity in Streptozotocin (STZ)-induced diabetic rats and the antioxidant effects of 3′,4′-Di-O-acetyl-cis-khellactone (DOAcK), as well as its toxic potential. We obtained DOAcK with an enantiomeric excess of 70% by chemical synthesis. Our results showed that this compound exerts an important antidiabetic effect: blood glucose decreased in groups treated with DOAcK by 60.9% at dose of 15?mg/kg (p?50) >2000?mg/kg and, at this dose, no signs of toxicity or death were reported after 14?days of observation. These results indicate that DOAcK can improve glucose metabolism, which may be due to the increased antioxidant activity of CAT, GPx and SOD. In addition, DOAcK is not toxic in the studies tested.