20107-13-5

Basic information

• Product Name: cis-Methylkhellactone
• Synonyms: cis-Methylkhellactone;(9R,10R)-9,10-Dihydro-9-hydroxy-10-methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one
• CAS NO: 20107-13-5
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28454
• Mol File: 20107-13-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: cis-Methylkhellactone(CAS DataBase Reference)
• NIST Chemistry Reference: cis-Methylkhellactone(20107-13-5)
• EPA Substance Registry System: cis-Methylkhellactone(20107-13-5)

Safety Data

• Hazardous Substances Data: 20107-13-5(Hazardous Substances Data)

Upstream product

• 96947-56-7 4'-angeloyloxy-3'-senecioyloxy-(-)-trans-khellactone 
• 80058-06-6 hystrixarin 
• 84458-88-8 campestrinol 
• 67-56-1 methanol 
• 870481-49-5 (+)-4'-decanoyl-cis-khellactone 

Relevant articles and documents

Coumarins from the fruits of Seseli devenyense

Eight new coumarins were isolated from the fruits of Seseli devenyense Simonkai. Their structures were established from NMR and mass data and their absolute configurations from chemical degradation correlation reactions. The new structures are the decanoic and dodecanoic esters of (+)-lomatin (3, 4), the decanoates of (+)-cis-khellactone at positions 4′ (5) and 3′ (6) as well as the 2′S epimer of 8-(2,3-dihydroxy-3-methylbutyl)-7- hydroxychromen-2-one (7) named devenyol, its two O-monoglucosides at positions 3′ and 7 named devenyosides A (8) and B (9), and the corresponding 3′- and 7-O-diglucoside named devenyoside C (10). This plant is an interesting example of stereochemical diversity based on biodiversity given that other members of the Apiaceae family produce exclusively the 2′R epimers of compounds 7-9.

Phytotoxic compounds from Prionosciadium watsoni

Bioassay-guided fractionation of a phytotoxic extract of Prionosciadium watsoni led to the isolation of three new pyranocoumarins and two pyranochromones. The new compounds were characterized as propionic acid (9R,10R)-9-acetoxy-8,8-dimethyl-9-10-dihydro-2H,8H-benzo[1,2-b:3,4-b ′]dipyran-2-one-10-yl ester (1), isobutyric acid (9R,10R)-9-hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4. b′]-dipyran-2-one-10-yl ester (2), isobutyric acid (9R)-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b′]dipyran-2 -one-9-yl ester (10), 2-methylbut-(2Z)-enoic acid (3R)-5-methoxy-3,4-dihydro-2,2,8-trimethyl-6-oxo-2H, 6H-benzo[1,2.b:5,4-b′]dipyran-3-yl ester (11), and isobutyric acid (3R)-5-methoxy-3,4-dihydro-2,2,8-trimethyl-6-oxo-2H,6H-benzo[1,2-b:5, 4-b′]dipyran-3-yl ester (12) by spectroscopic and chemical methods. The stereochemistry at the stereogenic centers was established by applying the Mosher ester methodology. The structures of 1 and 2 were corroborated by single-crystal X-ray diffraction studies. The phytotoxic activity of the isolated compounds was assessed on Amaranthus hypochondriacus, Echinochloa crus-galli, and Lemna pausicostata. The phytotoxins also modified the electrophoretic mobility of calmodulin from both bovine-brain and spinach.

COMPARATIVE CHARACTERIZATION OF THE COUMARIN COMPOSITION OF Seseli campestre GROWING IN MOLDAVIA AND IN THE CAUCASUS

The results are given of the identification of (-)-trans-khellactone and its 4'-methyl ether and (-)-3'(S),4'(S)-trans-3'-senecioyloxy-4'-angeloyloxy-3',4'-dihydroseselin and of the establishment of the structure of three new khellactone derivatives - campestrol (VII), C19H22O6, D20+32 deg (c 7.8; chloroform), campestrinol (X), C24H26O7, mp 116-118 deg C, and campestrinoside (I), C20H24O10, mp 172-173 deg C, D -272.5 deg (c 4.7; ethanol).It has been shown on the basis of chemical and spectral characteristics that campesol, earlier described as a new substance, is a mixture of two isomeric compounds - 4'-hydroxy-3'-senecioyloxy-3',4'-dihydroseselin and 3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin.