Paradol

Last updated
Paradol
Paradol.png
Names
Preferred IUPAC name
1-(4-Hydroxy-3-methoxyphenyl)decan-3-one
Other names
[6]-Paradol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.043.829 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 248-228-1
KEGG
MeSH C421614
PubChem CID
UNII
  • InChI=1S/C17H26O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h10,12-13,19H,3-9,11H2,1-2H3 X mark.svgN
    Key: CZNLTCTYLMYLHL-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C17H26O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h10,12-13,19H,3-9,11H2,1-2H3
    Key: CZNLTCTYLMYLHL-UHFFFAOYAE
  • CCCCCCCC(=O)CCC1=CC(=C(C=C1)O)OC
Properties
C17H26O3
Molar mass 278.39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Paradol is the active flavor constituent of the seeds of Guinea pepper ( Aframomum melegueta or grains of paradise). [1] It is also found in ginger. [2] Paradol has been found to have antioxidant and antitumor promoting effects in a mouse model. [3]

It is used in flavors as an essential oil to give spiciness.

See also

Related Research Articles

Zingiberaceae Family of plants

Zingiberaceae or the ginger family is a family of flowering plants made up of about 50 genera with a total of about 1600 known species of aromatic perennial herbs with creeping horizontal or tuberous rhizomes distributed throughout tropical Africa, Asia, and the Americas. Members of the family Zingiberaceae including turmeric, ginger, Javanese ginger, and galangal have been used for centuries in traditional medicine. Preclinical studies of Zingiberaceae extracts have shown analgesic properties.

<i>Aframomum melegueta</i> Species of flowering plant

Aframomum melegueta is a species in the ginger family, Zingiberaceae, and closely related to cardamom. Its seeds are used as a spice ; it imparts a pungent, black-pepper-like flavor with hints of citrus. It is commonly known as grains of paradise, melegueta pepper, alligator pepper, Guinea grains, ossame, or fom wisa. The term Guinea pepper has also been used, but is most often applied to Xylopia aethiopica.

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.

Quercetin Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; red onions and kale are common foods containing appreciable amounts of quercetin. Quercetin has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

An angiogenesis inhibitor is a substance that inhibits the growth of new blood vessels (angiogenesis). Some angiogenesis inhibitors are endogenous and a normal part of the body's control and others are obtained exogenously through pharmaceutical drugs or diet.

Theanine Chemical compound

Theanine, also known as L-γ-glutamylethylamide and N5-ethyl-L-glutamine, is an amino acid analogue of the proteinogenic amino acids L-glutamate and L-glutamine and is found primarily in particular plant and fungal species. It was discovered as a constituent of green tea in 1949; in 1950, it was isolated from gyokuro leaves. Theanine provides a unique brothy or savory (umami) flavor to green tea infusions.

Gingerol Chemical compound

Gingerol, properly as [6]-gingerol, is a phenol phytochemical compound found in fresh ginger that activates spice receptors on the tongue. Molecularly, gingerol is a relative of capsaicin and piperine, the compounds which are alkaloids, though the bioactive pathways are unconnected. It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.

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.

Seliciclib Chemical compound

Seliciclib is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors that preferentially inhibit multiple enzyme targets including CDK2, CDK7 and CDK9, which alter the growth phase or state within the cell cycle of treated cells. Seliciclib is being developed by Cyclacel.This is a phase II, dose ranging, multicenter, randomized, double-blind, placebo-controlled study.

<i>Kaempferia galanga</i> Species of flowering plant

Kaempferia galanga, commonly known as kencur, aromatic ginger, sand ginger, cutcherry, or resurrection lily, is a monocotyledonous plant in the ginger family, and one of four plants called galangal. It is found primarily in open areas in Indonesia, southern China, Taiwan, Cambodia, and India, but is also widely cultivated throughout Southeast Asia.

Vitamin D<sub>5</sub> Fat soluble vitamin

Precarious information de Vitamin D5 is a form of vitamin D.

Taxifolin Chemical compound

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

<i>Aframomum corrorima</i> species of plant in the family Zingiberaceae

Aframomum corrorima is a species of flowering plant in the ginger family, Zingiberaceae. It's a herbaceous perennial that produces leafy stems 1-2 meters tall from rhizomatous roots. The alternately-arranged leaves are dark green, 10-30 cm long and 2.5-6 cm across, elliptical to oblong in shape. Pink flowers are borne near the ground and give way to red, fleshy fruits containing shiny brown seeds, which are typically 3-5 mm in diameter.

Matrine

Matrine is an alkaloid found in plants from the genus Sophora. It has a variety of pharmacological effects, including anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism.

<i>Acmella oleracea</i> Species of flowering plant

Acmella oleracea is a species of flowering herb in the family Asteraceae. Common names include toothache plant, paracress, Sichuan buttons, buzz buttons, tingflowers and electric daisy. Its native distribution is unclear, but it is likely derived from a Brazilian Acmella species. It is grown as an ornamental and attracts fireflies when in bloom. It is used as a medicinal remedy in various parts of the world. A small, erect plant, it grows quickly and bears gold and red inflorescences. It is frost-sensitive but perennial in warmer climates.

Valorphin Chemical compound

Valorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH. It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin. Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals. It also possesses cytotoxic and antiproliferative properties against tumor cells, the mediation of which, because they are reversed by naloxone, appears to be dependent on the opioid receptors.

1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one is a natural product, a curcuminoid antioxidant found in turmeric and torch ginger.

Dicycloplatin

Dicycloplatin is a chemotherapy medication used to treat a number of cancers which includes the non-small-cell lung carcinoma and prostate cancer.

C-1027

C-1027 or Lidamycin is an antitumor antibiotic consisting of a complex of an enediyne chromophore and an apoprotein. It shows antibiotic activity against most Gram-positive bacteria. It is one of the most potent cytotoxic molecules known, due to its induction of a higher ratio of DNA double-strand breaks than single-strand breaks.

Aframomum daniellii, also known as African cardamom, is a species in the ginger family, Zingiberaceae. It was first described by Joseph Dalton Hooker, and got its current name from Karl Moritz Schumann.

References

  1. Xavier Fernandez; Christine Pintaric; Louisette Lizzani-Cuvelier; André-Michel Loiseau; Alain Morello & Patrick Pellerin (2006). "Chemical composition of absolute and supercritical carbon dioxide extract of Aframomum melegueta". Flavour and Fragrance Journal. 21 (1): 162–165. doi:10.1002/ffj.1554.
  2. Jolad SD, Lantz RC, Chen GJ, Bates RB, Timmermann BN (2005). "Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production". Phytochemistry. 66 (13): 1614–1635. doi:10.1016/j.phytochem.2005.05.007. PMID   15996695.
  3. Chung WY, Jung YJ, Surh YJ, Lee SS, Park KK (2001). "Antioxidative and antitumor promoting effects of [6]-paradol and its homologs". Mutat. Res. 496 (1–2): 199–206. doi:10.1016/s1383-5718(01)00221-2. PMID   11551496.