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Preferred IUPAC name 1,3,8-Trihydroxyanthracene-9,10-dione | |
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3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C14H8O5 | |
Molar mass | 256.210 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,3,8-Trihydroxyanthraquinone is an organic compound. It is one of many trihydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of three hydrogen atoms by hydroxyl (OH) groups.
The compound occurs in some microorganisms [1] and in alcoholic extracts of the wood of the South American plant Senna reticulata (mangerioba grande or maria mole in Portuguese), used in the local folk medicine for liver problems and rheumatism. The extract also contained, among other products chrysophanol (1,8-dihydroxy-3-methylanthraquinone), physcion (1,8-dihydroxy-3-methyl-6-methoxyanthraquinone), aloe-emodin (3-carbinol-1,8-dihydroxyanthraquinone), lunatin (3-methoxy-1,6,8-trihydroxyanthraquinone), emodin (6-methyl-1,3,8-trihydroxyanthraquinone), and chrysophanol-10,10'-bianthrone. [1]
The substance is soluble in ethanol and chloroform but not in n-hexane, and melts at 283 °C. [1]
Persicaria odorata, with common names Vietnamese coriander, rau răm, laksa leaf, Vietnamese cilantro, phak phai, praew leaf, hot mint and Cambodian mint, is a herb whose leaves are used in Southeast Asian and Northeast Indian cooking.
A methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3. On a benzene ring, the Hammett equation classifies a methoxy substituent at the para position as an electron-donating group, but as an electron-withdrawing group if at the meta position. At the ortho position, steric effects are likely to cause a significant alteration in the Hammett equation prediction which otherwise follows the same trend as that of the para position.
Bauhinia purpurea is a species of flowering plant in the family Fabaceae, native to the Indian subcontinent and Myanmar, and widely introduced elsewhere in tropical and subtropical areas of the world. Common names include orchid tree, purple bauhinia, camel's foot, butterfly tree, and Hawaiian orchid tree.
For the parent molecule 9,10-anthraquinone, see anthraquinone
Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.
Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum Palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schuttgelb, and Persian Berry Lake.
Aloe emodin is an anthraquinone and an isomer of emodin present in aloe latex, an exudate from the aloe plant. It has a strong stimulant-laxative action. Aloe emodin is not carcinogenic when applied to the skin, although it may increase the carcinogenicity of some kind of radiation.
Aegiceras corniculatum, commonly known as black mangrove, river mangrove, goat's horn mangrove, or khalsi, is a species of shrub or tree mangrove in the primrose family, Primulaceae, with a distribution in coastal and estuarine areas ranging from India through South East Asia to southern China, New Guinea and Australia.
Senna reticulata, the mangerioba grande or maria mole in Portuguese, is a pioneer tree species found on highly fertile floodplains in South America. It has some medicinal uses, but is regarded by farmers as a noxious weed, named matapasto due to its ability to grow fast and outshade neighbouring plants.
Senna occidentalis [Indian vernacular name Usaya ki Fali] is a pantropical plant species, native to the Americas. The species was formerly placed in the genus Cassia.
Naphthoquinone is a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones:
Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone. It is a C-3 methyl substituted chrysazin of the trihydroxyanthraquinone family.
Homoisoflavonoids (3-benzylidenechroman-4-ones) are a type of phenolic compounds occurring naturally in plants.
Lunatin (3-methoxy-1,6,8-trihydroxyanthraquinone) is a derivative of anthraquinone. It is produced by the Senna reticulata tree and can be extracted by soaking the bark in alcohol. Lunatin is also produced by the fungus Curvularia lunata which inhabits a marine sponge. Lunatin is an antibacterial substance.
Ploiarium is a genus of three species of woody plants in the family Bonnetiaceae. It is native to tropical forests and peat swamp forests in Southeast Asia including southern Indochina, Malay Peninsula, Sumatra, and Borneo. Species are generally slow growing with irregular flowering and fruiting cycles. Colonization of plants by arbuscular mycorrhizal fungi is known to improve growth and biomass.
Garcinia pseudoguttifera, known as the mo'onia tree in its native range, is a species of flowering tree in the family Clusiaceae or Guttiferae.
Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol. It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in Cannabis sativa, but can also be produced synthetically by hydrogenation of cannabis extracts. HHC was first synthesized in 1947 by Roger Adams using natural THC found in Cannabis sativa. Several research groups have successfully synthesized (+)-HHC and (-)-HHC using citronellal and olivetol, as well as other related compounds. While similar compounds have previously been identified in cannabis, hexahydrocannabinol itself has rarely been isolated from the plant. The de Las Heras group in 2020 took lipid extract from Cannabis sativa seeds and discovered 43 cannabinoids in the crude extract; one of them being hexahydrocannabinol. It has two diastereomers at the methyl (9) position. HHC is typically made from Δ8-THC, or Δ9-THC. There are no double bonds in the cyclohexyl ring like D8/D9 have—they have been removed from the structure and hydrogens have been added to the compound. Similar structural analogs of HHC has been demonstrated to bind to the CB1 receptor and produces cannabinoid effects in animals, with the 9β-HHC enantiomer being much more active than 9α-HHC. While HHC has been shown to bind to the CB1 receptor, it binds with weaker affinity than THC, which has typically been an indication that it is not as intoxicating as typical THC. Since HHC is found naturally in the cannabis plant, humans have likely been unknowingly consuming small amounts of this cannabinoid for centuries.
Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in many lichens, and it is important in the taxonomy of species in several genera, such as Pertusaria and Pyxine. More than a dozen lichen species have a variation of the word lichexanthone incorporated as part of their binomial name. The presence of lichexanthone in lichens causes them to fluoresce a greenish-yellow colour under long-wavelength UV light; this feature is used to help identify some species. Lichexanthone is also found in several plants, and some species of fungi that do not form lichens.
Dianella ensifolia is a flowering plant, of the family Asphodelaceae. It is native to southern China, India, Japan, Madagascar, Malesia, the Pacific Islands, Singapore, Sri Lanka, Taiwan, and tropical Asia. Its common names include umbrella dracaena, common dianella, siak-siak, and flax lily.