Dillapiole

Last updated
Dillapiole
Dillapiole structure.svg
Dillapiole-3D-balls.png
Names
Preferred IUPAC name
4,5-Dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Other names
6-Allyl-4,5-dimethoxybenzo[d][1,3]dioxole
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.149.911 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 621-020-1
KEGG
PubChem CID
UNII
  • InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3 Yes check.svgY
    Key: LIKYNOPXHGPMIH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3
    Key: LIKYNOPXHGPMIH-UHFFFAOYAI
  • O1c2cc(c(OC)c(OC)c2OC1)CC=C
Properties
C12H14O4
Molar mass 222.240 g·mol−1
Density 1.163 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Dillapiole is an organic chemical compound and essential oil commonly extracted from dill weed, though it can be found in a variety of other plants such as fennel root. [1] This compound is closely related to apiole, having a methoxy group positioned differently on the benzene ring. [2] [3] Dillapiole works synergically with certain insecticides like pyrethrins similarly to piperonyl butoxide, which likely results from inhibition of the MFO enzyme of insects. [4]

No carcinogenicity was detected with parsley apiol or dill apiol in mice. [5]

Related Research Articles

Dill Species of flowering plant in the celery family Apiaceae

Dill is an annual herb in the celery family Apiaceae. It is the only species in the genus Anethum. Dill is grown widely in Eurasia, where its leaves and seeds are used as a herb or spice for flavouring food.

Thujone Group of four possible stereoisomers found in various plants: a.o., absinthe and mint

Thujone is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.

Lavender oil Essential oil distilled from lavender flower spikes

Lavender oil is an essential oil obtained by distillation from the flower spikes of certain species of lavender. There are over 400 types of lavender species worldwide with different scents and qualities. Two forms are distinguished, lavender flower oil, a colorless oil, insoluble in water, having a density of 0.885 g/mL; and lavender spike oil, a distillate from the herb Lavandula latifolia, having density 0.905 g/mL. Like all essential oils, it is not a pure compound; it is a complex mixture of phytochemicals, including linalool and linalyl acetate.

Safrole Chemical compound

Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.

Myristicin

Myristicin is a naturally occurring compound found in common herbs and spices, the most well known being nutmeg. It is an insecticide, and has been shown to enhance the effectiveness of other insecticides in combination. Myristicin is also a precursor for substituted amphetamine derivative compounds structurally related to MMDA and MDMA; it is believed to be metabolized in the liver into MMDA, but unlikely since no MMDA was found in urine, in the body it produce hallucinogenic effects, and can be converted to MMDMA in controlled chemical synthesis. It interacts with many enzymes and signaling pathways in the body, is cytotoxic to living cells, and may also have chemoprotective properties.

Thymol Chemical compound found in plants including thyme

Thymol, C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris, ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris.

Eugenol Chemical compound

Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.

Anethole Chemical compound

Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, abundant in tarragon (Asteraceae) and basil (Lamiaceae), that has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water, the ouzo effect.

Carvone Chemical compound

Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway, spearmint, and dill.

Apiole Chemical compound

Apiole is a phenylpropene, also known as apiol, parsley apiol, or parsley camphor. Its chemical name is 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. It is found in the essential oils of celery leaf and all parts of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation.

Eucalyptol Chemical compound

Eucalyptol is a monoterpenoid. A colorless liquid, it is a bicyclic ether. Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up 90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

Caryophyllene Chemical compound

Caryophyllene, more formally (−)-β-caryophyllene, (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

Humulene Chemical compound

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

<i>alpha</i>-Pinene Chemical compound

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary and Satureja myrtifolia. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

Phenylpropanoid

The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

DMMDA

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours. He reported DMMDA as producing LSD-like images, mydriasis, ataxia, and time dilation.

α-Cadinol Chemical compound

α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol.

Nothoapiole Chemical compound

Nothoapiole is a phenylpropene, a natural organic compound present in the essential oil of Perilla frutescens from Jeju Island in Korea and the major component of the essential oil obtained from the roots of Pleurospermum angelicoides Benth. It is also found in the essential oil of black caraway fruits and Carum nigrum.

Bornyl acetate Chemical compound

Bornyl acetate is a chemical compound. Its molecular formula is C12H20O2 and its molecular weight is 196.29 g/mol. It is the acetate ester of borneol. It is used as a food additive, flavouring agent, and odour agent.

References

  1. Azeez, Shamina (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 227–241 [230]. ISBN   9781845934057.
  2. Santos, P. A. G.; Figueiredo, A. C.; Lourenço, P. M. L.; Barroso, J. G.; Pedro, L. G.; Oliveira, M. M.; Schripsema, J.; Deans, S. G.; Scheffer, J. J. C. (2002). "Hairy root cultures of Anethum graveolens (Dill): Establishment, growth, time-course study of their essential oil and its comparison with parent plant oils". Biotechnology Letters. 24 (12): 1031–1036. doi:10.1023/A:1015653701265. S2CID   10120732.
  3. Shulgin, A. T.; Sargent, T. (1967). "Psychotrophic phenylisopropylamines derived from apiole and dillapiole". Nature. 215 (5109): 1494–1495. Bibcode:1967Natur.215.1494S. doi:10.1038/2151494b0. PMID   4861200. S2CID   26334093.
  4. INpatent 128,129,Mankombu Sambasivan Swaminathan,"Improvements in or relating to methylenedioxyphenyl derivatives",published 1970-08-21,issued 1970-10-24
  5. Phillips, David H.; Reddy, M. Vijayaraj; Randerath, Kurt (1984). "32P-Post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice". Carcinogenesis. 5 (12): 1623–1628. doi:10.1093/carcin/5.12.1623. PMID   6499113.

See also