Names | |
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IUPAC name Lup-20(29)-ene-3β,28-diol | |
Systematic IUPAC name (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol | |
Other names Betulinol, betuline, betulol, betulinic alcohol, trochol | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.797 |
EC Number |
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KEGG | |
PubChem CID | |
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Properties | |
C30H50O2 | |
Molar mass | 442.728 g·mol−1 |
Appearance | solid with needle-like crystals [1] |
Melting point | 256 to 257 °C (493 to 495 °F; 529 to 530 K) |
insoluble [1] | |
Solubility | slightly soluble in ethanol and benzene; soluble in diethyl ether, ethyl acetate and ligroin [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees. It forms up to 30% of the dry weight of silver birch bark. [2] It is also found in birch sap.[ citation needed ] Inonotus obliquus contains betulin. [3]
The compound in the bark gives the tree its white color which appears to protect the tree from mid-winter overheating by the sun. As a result, birches are some of the northernmost occurring deciduous trees.
Betulin was discovered in 1788 by German-Russian chemist Johann Tobias Lowitz. [4] [5]
Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28.
A birch is a thin-leaved deciduous hardwood tree of the genus Betula, in the family Betulaceae, which also includes alders, hazels, and hornbeams. It is closely related to the beech-oak family Fagaceae. The genus Betula contains 30 to 60 known taxa of which 11 are on the IUCN 2011 Red List of Threatened Species. They are a typically rather short-lived pioneer species widespread in the Northern Hemisphere, particularly in northern areas of temperate climates and in boreal climates. Birch wood, the wood of the birch, is used for a wide range of purposes.
Bark is the outermost layer of stems and roots of woody plants. Plants with bark include trees, woody vines, and shrubs. Bark refers to all the tissues outside the vascular cambium and is a nontechnical term. It overlays the wood and consists of the inner bark and the outer bark. The inner bark, which in older stems is living tissue, includes the innermost layer of the periderm. The outer bark on older stems includes the dead tissue on the surface of the stems, along with parts of the outermost periderm and all the tissues on the outer side of the periderm. The outer bark on trees which lies external to the living periderm is also called the rhytidome.
Betula pendula, commonly known as silver birch, warty birch, European white birch, or East Asian white birch, is a species of tree in the family Betulaceae, native to Europe and parts of Asia, though in southern Europe, it is only found at higher altitudes. Its range extends into Siberia, China, and southwest Asia in the mountains of northern Turkey, the Caucasus, and northern Iran. It has been introduced into North America, where it is known as the European white birch or weeping birch and is considered invasive in some states in the United States and parts of Canada. The tree can also be found in more temperate regions of Australia.
Betula pubescens, commonly known as downy birch and also as moor birch, white birch, European white birch or hairy birch, is a species of deciduous tree, native and abundant throughout northern Europe and northern Asia, growing farther north than any other broadleaf tree. It is closely related to, and often confused with, the silver birch, but grows in wetter places with heavier soils and poorer drainage; smaller trees can also be confused with the dwarf birch.
Boron carbide (chemical formula approximately B4C) is an extremely hard boron–carbon ceramic, a covalent material used in tank armor, bulletproof vests, engine sabotage powders, as well as numerous industrial applications. With a Vickers hardness of >30 GPa, it is one of the hardest known materials, behind cubic boron nitride and diamond.
A bark beetle is the common name for the subfamily of beetles Scolytinae. Previously, this was considered a distinct family (Scolytidae), but is now understood to be a specialized clade of the "true weevil" family (Curculionidae). Although the term "bark beetle" refers to the fact that many species feed in the inner bark (phloem) layer of trees, the subfamily also has many species with other lifestyles, including some that bore into wood, feed in fruit and seeds, or tunnel into herbaceous plants. Well-known species are members of the type genus Scolytus, namely the European elm bark beetle S. multistriatus and the large elm bark beetle S. scolytus, which like the American elm bark beetle Hylurgopinus rufipes, transmit Dutch elm disease fungi (Ophiostoma). The mountain pine beetle Dendroctonus ponderosae, southern pine beetle Dendroctonus frontalis, and their near relatives are major pests of conifer forests in North America. A similarly aggressive species in Europe is the spruce ips Ips typographus. A tiny bark beetle, the coffee berry borer, Hypothenemus hampei is a major pest on coffee plantations around the world.
The Hymenochaetales are an order of fungi in the class Agaricomycetes. The order in its current sense is based on molecular research and not on any unifying morphological characteristics. According to one 2008 estimate, the Hymenochaetales contain around 600 species worldwide, mostly corticioid fungi and poroid fungi, but also including several clavarioid fungi and agarics. Species of economic importance include wood decay fungi in the genera Phellinus and Inonotus sensu lato, some of which may cause losses in forestry. Therapeutic properties are claimed for Inonotus obliquus ("chaga") and Phellinus linteus, both of which are now commercially marketed.
Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Birch bark or birchbark is the bark of several Eurasian and North American birch trees of the genus Betula.
A sclerotium, is a compact mass of hardened fungal mycelium containing food reserves. One role of sclerotia is to survive environmental extremes. In some higher fungi such as ergot, sclerotia become detached and remain dormant until favorable growth conditions return. Sclerotia initially were mistaken for individual organisms and described as separate species until Louis René Tulasne proved in 1853 that sclerotia are only a stage in the life cycle of some fungi. Further investigation showed that this stage appears in many fungi belonging to many diverse groups. Sclerotia are important in the understanding of the life cycle and reproduction of fungi, as a food source, as medicine, and in agricultural blight management.
Inonotus obliquus, commonly called chaga, is a fungus in the family Hymenochaetaceae. It is parasitic on birch and other trees. The sterile conk is irregularly formed and resembles burnt charcoal. It is not the fruiting body of the fungus, but a sclerotium or mass of mycelium, mostly black because of a substantial amount of melanin.
Inonotus hispidus, commonly known as shaggy bracket, is a fungus and a plant pathogen. This fungus has been used in eastern Asia as a popular remedy for many illnesses like cancer, diabetes, and other stomach ailments. In modern pharmacology, it has aided in lowering blood glucose levels, showing anti-tumor responses and improving overall health in mice.
Yuremamine is a phytoindole alkaloid which was isolated from the bark of Mimosa tenuiflora in 2005, and erroneously assigned a pyrrolo[1,2-a]indole structure that was thought to represent a new class of indole alkaloids. However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative. It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, but total synthesis revealed that yuremamine as a free base is colorless, and the formation of a trifluoroacetate salt during HPLC purification is what led to the purple appearance.
Forest dieback is a condition in trees or woody plants in which peripheral parts are killed, either by pathogens, parasites or conditions like acid rain, drought, and more. These episodes can have disastrous consequences such as reduced resiliency of the ecosystem, disappearing important symbiotic relationships and thresholds. Some tipping points for major climate change forecast in the next century are directly related to forest diebacks.
Birch bark tar is a substance that is synthesized by dry distillation of birch tree bark.
Inotodiol is an anti-inflammatory sterol isolated from Inonotus obliquus.
Trametenolic acid is an anti-inflammatory sterol isolated from Inonotus obliquus.
Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.
Medicinal fungi are fungi that contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.
Suberinic acids are a type of carboxylic acids naturally encountered in the bark of Betula tree species. Chemically, they predominantly have long (C18) chains with α- and ω- bifunctional saturated and unsaturated fatty acid ends. Their name originates from suberin, a major chemical biopolymer of tree bark.