Thujaplicinol
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Thujaplicinol
Thujaplicinol is either of two isomeric tropolone-related natural products. They are found in tree species primarily in bark, needles, xylem, of the family of ''Cupressaceae'' like the ''Cupressus, Thuja, Juniperus'' and ''Thujopsis''. The thujaplicinols are structurally equivalent to the thujaplicins with an additional hydroxyl group. They belong to the class of natural terpenoids having two free hydroxyl groups at C3 and C5 position. The thujaplicinols are highly volatile compounds. It is known that the presence of such tropolones, including alpha-tropolone and its isopropyl derivatives, result in the high natural durability of wood species, such as western red cedar, juniper and cypress Cypress is a common name for various coniferous trees or shrubs from the ''Cupressus'' genus of the '' Cupressaceae'' family, typically found in temperate climates and subtropical regions of Asia, Europe, and North America. The word ''cypress'' .... Uses ''Alpha-thujaplicinol'', an isom ...
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Tropolone
Tropolone is an organic compound with the chemical formula . It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position. Synthesis and reactions Many methods have been described for the synthesis of tropolone. One involves bromination of 1,2-cycloheptanedione with ''N''-bromosuccinimide followed by dehydrohalogenation at elevated temperatures, while another uses acyloin condensation of the ethyl ester of pimelic acid the acyloin again followed by oxidation by bromine. : An alternate route is a +2 cycloaddition of cyclopentadiene with a ketene to give a bicyclo .2.0eptyl structure, followed by hydrolysis and breakage of the fusion bond to give the single ring: : Thy hydroxyl group of tropolone is acidic, having a ...
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Cupressaceae
Cupressaceae or the cypress family is a family of conifers. The family includes 27–30 genera (17 monotypic), which include the junipers and redwoods, with about 130–140 species in total. They are monoecious, subdioecious or (rarely) dioecious trees and shrubs up to tall. The bark of mature trees is commonly orange- to red-brown and of stringy texture, often flaking or peeling in vertical strips, but smooth, scaly or hard and square-cracked in some species. The family reached its peak of diversity during the Mesozoic era. Description The leaves are arranged either spirally, in decussate pairs (opposite pairs, each pair at 90° to the previous pair) or in decussate whorls of three or four, depending on the genus. On young plants, the leaves are needle-like, becoming small and scale-like on mature plants of many genera; some genera and species retain needle-like leaves throughout their lives. Old leaves are mostly not shed individually, but in small sprays of foliage ( clad ...
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Thujaplicin
Thujaplicin (isopropyl cycloheptatrienolone) is any of three isomeric tropolone-related natural products that have been isolated from the softwoods of the trees of ''Cupressaceae'' family. These compounds are known for their antibacterial, antifungal, and antioxidant properties. They were the first natural tropolones to be made synthetically. History Thujaplicins were discovered in the mid-1930s and purified from the heartwood of ''Thuja plicata'' Donn ex D. Don, commonly called as Western red cedar tree. These compounds were also identified in the constituents of ''Chamaecyparis obtusa'', another species from the ''Cupressaceae'' family. ''C. obtusa'' is native to East Asian countries including Japan and Taiwan, and is also known as ''Taiwan hinoki'', from which the β-thujaplicin was first isolated in 1936 and received its name, ''hinokitiol''. Thujaplicins were the first natural tropolones to be made synthetically, by Ralph Raphael and colleagues, and the β-thujaplicin w ...
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Western Red Cedar
''Thuja plicata'' is a large evergreen coniferous tree in the family Cupressaceae, native to the Pacific Northwest of North America. Its common name is western redcedar in the U.S. or western red cedar in the UK, and it is also called pacific red cedar, giant arborvitae, western arborvitae, just cedar, giant cedar, or shinglewood. It is not a true cedar of the genus ''Cedrus''. ''T. plicata'' is the largest species in the genus ''Thuja'', growing up to tall and in diameter. It mostly grows in areas that experience a mild climate with plentiful rainfall, although it is sometimes present in drier areas on sites where water is available year-round, such as wet valley bottoms and mountain streamsides. The species is shade-tolerant and able to establish in forest understories and is thus considered a climax species. It is a very long-lived tree, with some specimens reaching ages of well over 1,000 years. Indigenous peoples of the Pacific Northwest use the wood of this species for ma ...
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Thujopsis Dolabrata
''Thujopsis'' () is a genus of conifers in the cypress family (Cupressaceae), the sole member of which is ''Thujopsis dolabrata''. It is endemic to Japan, where it is known as ''asunaro'' (). It is similar to the closely related genus ''Thuja'' (arborvitae), differing in its broader, thicker leaves and cones. Etymology A popular allegory for the etymology of ''asunaro'' is ''asu wa hinoki ni narou'' (), literally "tomorrow it will become a hinoki cypress", i.e. the tree looks like a smaller version of the common hinoki cypress. In Japan, it is also known as ''hiba'' (), among many regional variations: asunaro is called ''ate'' () in Ishikawa, ''atebi'' on Sado Island, among other names. Outside of Japan, it is also known as false arborvitae or hiba arborvitae. Description ''Thujopsis'' is a medium to large evergreen tree, reaching up to 40 m tall and 1.5 m trunk diameter, with red-brown bark which peels in vertical strips. The leaves are arranged in decussate pairs, scal ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the existence or possibility of isomers. Isomers do not necessarily share similar chemical property, chemical or physical property, physical properties. Two main forms of isomerism are structural isomerism, structural (or constitutional) isomerism, in which ''chemical bond, bonds'' between the atoms differ; and stereoisomerism (or spatial isomerism), in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different Isotopologue, isotopologues. The depth of analy ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets). The term ''natural product'' has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized meta ...
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Hydroxyl Group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this ...
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Terpenoid
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic compound, organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known Natural Products, natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists. Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. Well-known terpenoids include citral, menthol, camphor, salvin ...
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Cypress
Cypress is a common name for various coniferous trees or shrubs from the ''Cupressus'' genus of the '' Cupressaceae'' family, typically found in temperate climates and subtropical regions of Asia, Europe, and North America. The word ''cypress'' is derived from Old French ''cipres'', which was imported from -4; we might wonder whether there's a point at which it's appropriate to talk of the beginnings of French, that is, when it wa ... ''cipres'', which was imported from Latin ''cypressus'', the latinisation of the Greek language">Greek κυπάρισσος (''kyparissos''). The name derives from Cyparissus, a mythological figure who was turned into a tree after killing a stag. Description Cypress trees typically reach heights of up to and exhibit a pyramidal form, particularly in their youth. Many are characterised by their needle-like, evergreen foliage and acorn-like seed cones. Some species develop flattened, spreading heads at maturity, while certain variants may manife ...
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Natural Products
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets). The term ''natural product'' has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metab ...
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Monoterpenes
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries. Biosynthesis Monoterpenes are derived biosynthetically from units of isopentenyl pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP-(2-methyl-D-erythritol-4-phosphate) pathway, which is initiated from C5 sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precurs ...
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