Acevaltrate

Last updated
Acevaltrate
Acevaltrate.svg
Names
Preferred IUPAC name
(1S,2′R,6S,7aS)-4-[(Acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2′-oxiran]-6-yl 3-(acetyloxy)-3-methylbutanoate
Other names
Acetoxyvaltrate; Acetovaltrate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.042.426 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 246-685-1
PubChem CID
UNII
  • InChI=1S/C24H32O10/c1-13(2)7-19(27)33-22-21-17(16(11-30-22)10-29-14(3)25)8-18(24(21)12-31-24)32-20(28)9-23(5,6)34-15(4)26/h8,11,13,18,21-22H,7,9-10,12H2,1-6H3/t18-,21+,22-,24+/m0/s1
    Key: FWKBQAVMKVZEOT-STCFVSJZSA-N
  • InChI=1/C24H32O10/c1-13(2)7-19(27)33-22-21-17(16(11-30-22)10-29-14(3)25)8-18(24(21)12-31-24)32-20(28)9-23(5,6)34-15(4)26/h8,11,13,18,21-22H,7,9-10,12H2,1-6H3/t18-,21+,22-,24+/m0/s1
    Key: FWKBQAVMKVZEOT-STCFVSJZBV
  • CC(C)CC(=O)O[C@H]1[C@H]2C(=C[C@@H]([C@]23CO3)OC(=O)CC(C)(C)OC(=O)C)C(=CO1)COC(=O)C
Properties
C24H32O10
Molar mass 480.510 g·mol−1
Melting point 80–81 °C (176–178 °F; 353–354 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acevaltrate is an iridoid isolated from Valeriana glechomifolia . [2]

Related Research Articles

<span class="mw-page-title-main">Valerian (herb)</span> Species of flowering plant

Valerian is a perennial flowering plant native to Europe and Asia. In the summer when the mature plant may have a height of 1.5 metres, it bears sweetly scented pink or white flowers that attract many fly species, especially hoverflies of the genus Eristalis. It is consumed as food by the larvae of some Lepidoptera species, including the grey pug.

<span class="mw-page-title-main">Nepetalactone</span> Chemical compound

Nepetalactone is a name for multiple iridoid analog stereoisomers. Nepetalactones are produced by Nepeta cataria (catnip) and many other plants belonging to the genus Nepeta, in which they protect these plants from herbivorous insects by functioning as insect repellents. They are also produced by many aphids, in which they are sex pheromones. Nepetalactones are cat attractants, and cause the behavioral effects that catnip induces in domestic cats. However, they affect visibly only about two thirds of adult cats. They produce similar behavioral effects in many other felids, especially in lions and jaguars. In 1941, the research group of Samuel M. McElvain was the first to determine the structures of nepetalactones and several related compounds.

<i>Junonia coenia</i> Species of insect (butterfly)

Junonia coenia, known as the common buckeye or buckeye, is a butterfly in the family Nymphalidae. Its range covers much of North America and some of Central America, including most of the eastern half of the US, the lower to middle Midwest, the Southwest, southern Canada, and Mexico. Its habitat is open areas with low vegetation and some bare ground. Its original ancestry has been traced to Africa, which then experiences divergence in Asia. The species Junonia grisea, the gray buckeye, is found west of the Rocky Mountains and was formerly a subspecies of Junonia coenia.

<span class="mw-page-title-main">Actinidine</span> Chemical compound

Actinidine is an iridoid produced in nature by a wide variety of plants and animals. It was the first cyclopentanoid monoterpene alkaloid to be discovered. It is one of several compounds that may be extracted from the valerian root and silver vine, as well as several types of insects in the larval and imaginal stages. Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.

<span class="mw-page-title-main">Genipin</span> Chemical compound

Genipin is a chemical compound found in Genipa americana fruit extract. It is an aglycone derived from an iridoid glycoside called geniposide which is also present in fruit of Gardenia jasminoides.

<span class="mw-page-title-main">Iridoid</span> Class of chemical compounds

Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose.

<span class="mw-page-title-main">Isovaleramide</span> Chemical compound

Isovaleramide is an organic compound with the formula (CH3)2CHCH2C(O)NH2. The amide derived from isovaleric acid, it is a colourless solid.

A cat pheromone is a chemical molecule, or compound, that is used by cats and other felids for communication. These pheromones are produced and detected specifically by the body systems of cats and evoke certain behavioural responses.

<span class="mw-page-title-main">Catnip</span> Nepeta cataria; species of plant

Nepeta cataria, commonly known as catnip, catswort, catwort, and catmint, is a species of the genus Nepeta in the family Lamiaceae, native to southern and eastern Europe, the Middle East, Central Asia, and parts of China. It is widely naturalized in northern Europe, New Zealand, and North America. The common name catmint can also refer to the genus as a whole.

<i>Cornus officinalis</i> Species of flowering plant

Cornus officinalis, the Japanese cornel or Japanese cornelian cherry, is a species of flowering plant in the dogwood family Cornaceae. Despite its name, it is native to China and Korea as well as Japan. It is not to be confused with C. mas, which is also known as the Cornelian cherry. It is not closely related to the true cherries of the genus Prunus.

<i>Actinidia polygama</i> Species of plant

Actinidia polygama is a species of kiwifruit in the Actinidiaceae family. It grows in the mountainous areas of Korea, Japan and China at elevations between 500 and 1,900 metres.

<span class="mw-page-title-main">Catalpol</span> Chemical compound

Catalpol is an iridoid glucoside. This natural product falls in the class of iridoid glycosides, which are simply monoterpenes with a glucose molecule attached.

<span class="mw-page-title-main">Aucubin</span> Chemical compound

Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.

<span class="mw-page-title-main">Deacetylasperulosidic acid</span> Chemical compound

Deacetylasperulosidic acid is an iridoid compound found in a few medicinal plants, such as Morinda citrifolia. Some in vitro and in vivo bioactivities of deacetylasperulosidic acid include anti-inflammatory, analgesic, anti-cancer, antioxidant, anti-arthritic, anti-mutagenic, anti-clastogenic, and hepatoprotection.

<i>Valeriana celtica</i> Species of flowering plant

Valeriana celtica is a species of plant in the family Caprifoliaceae. It is also known as Alpine valerian and valerian spikenard. It is endemic to the Eastern Alps and to the Graian and Pennine Alps. It grows as a perennial herb 5 to 15 cm (2.0–5.9 in) tall. Along with Valeriana saxatilis and Valeriana elongata, it forms a clade of dioecious plants. Until the 1930s, it was extensively harvested for export to Asia for use in perfumes. The root has been used as a folk remedy as a nerve tonic.

<span class="mw-page-title-main">Verbascoside</span> Chemical compound

Verbascoside is a caffeoyl phenylethanoid glycoside in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

Valerena-4,7(11)-diene synthase is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Nepetalactol</span> Chemical compound

Nepetalactol is an iridoid. It is produced from 8-oxogeranial by the enzyme iridoid synthase. Nepetalactol is a substrate for the enzyme iridoid oxidase (IO) which produces 7-deoxyloganetic acid. It has been identified in Actinidia polygama as a major cat attractant, and a mosquito repellent. The fact that mosquitos bite cats with nepetalactol on their fur less often may explain why cats are attracted to silver vine in the first place.

<span class="mw-page-title-main">Iridodial</span> Chemical compound

Iridodial is an iridoid. It is produced from 8-oxogeranial by the enzyme iridoid synthase (IS). Iridodial is one of the substrates for the enzyme iridoid oxidase (IO) which produces 7-deoxyloganetic acid.

<i>Valeriana dioica</i> Species of plant in the genus Valeriana

Valeriana dioica, the marsh valerian, is a species of flowering plant in the genus Valeriana, native to Europe and Anatolia. It is typically found in calcareous fens. It is a dioecious species, with male and female flowers on separate individuals, and it is pollinated by small flies.

References

  1. Huang, Bao-Kang; Qin, Lu-Ping; Liu, Yu-Ming; Zhang, Qiao-Yan; Zheng, Han-Chen (14 August 2009). "Sesquiterpene and iridoids from Valeriana pseudofficinalis roots". Chemistry of Natural Compounds. 45 (3): 363–366. doi:10.1007/s10600-009-9344-8. S2CID   9531804.
  2. Bettero, GM; Salles, L; Rosário Figueira, RM; Poser, Gv; Rates, SM; Noël, F; Quintas, LE (2011). "In vitro effect of valepotriates isolated from Valeriana glechomifolia on rat P-type ATPases". Planta Medica. 77 (15): 1702–6. doi:10.1055/s-0030-1271084. PMID   21567360. S2CID   260284677.