19380-05-3

Basic information

• Product Name: (9R)-8,8-Dimethyl-9,10-dihydro-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-ol
• Synonyms: (+)-Lomatin;(9R)-8,8-Dimethyl-9,10-dihydro-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-ol;(9R)-8,8-Dimethyl-9α-hydroxy-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one;(R)-9,10-Dihydro-9-hydroxy-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one;Lomatin
• CAS NO: 19380-05-3
• Molecular Formula: C14H14O4
• Molecular Weight: 246.25856
• Mol File: 19380-05-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (9R)-8,8-Dimethyl-9,10-dihydro-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (9R)-8,8-Dimethyl-9,10-dihydro-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-ol(19380-05-3)
• EPA Substance Registry System: (9R)-8,8-Dimethyl-9,10-dihydro-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-ol(19380-05-3)

Safety Data

• Hazardous Substances Data: 19380-05-3(Hazardous Substances Data)

Upstream product

• 2221-67-2 3'-keto,3',4'-dihydroseselin 
• 518-76-3 (±)-cis-khellactone 
• 484-14-0 osthenol 
• 1269599-04-3 C₁₄H₁₄O₄ 
• 1196892-20-2 C₂₀H₂₈O₄Si 
• 1161258-85-0 7-(tert-butyldimethylsilyloxy)-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 
• 870481-48-4 (+)-dodecanoyllomatin 
• 870481-47-3 (+)-decanoyllomatin 
• 1147-25-7 lomatin 
• 1165-60-2 (-)-O-angeloyllomatin 
• 141243-21-2 (+)-lomatin-3'-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabinohexopyranoside) 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 27421-19-8 7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one 
• 27421-18-7 7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one 

Downstream Products

• 15885-51-5 selinidin 
• 1165-60-2 (-)-O-angeloyllomatin 

Relevant articles and documents

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.

Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC50 value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5- methoxypsoralen (35), 8-geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC50 values 25.0 μM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

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.