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Patchoulol
Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli. Patchouli oil is an important material in perfumery. The (−)- optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is also used in the synthesis of the chemotherapy drug Taxol. Structure determination Patchouli alcohol was first isolated in 1869 by Gal and its chemical composition later correctly formulated as C15H26O by Montgolfier. During early structural investigation the presence of a saturated tricyclic tertiary alcohol was established. After several years of careful study Büchi and co-workers proposed the structure of patchouli alcohol to correspond to 1, based on degradation studies from his earlier work, verified later by synthesis of material which corresponded to the natural authentic sample of patchouli alcohol. A serendipitous finding by Dunitz and co-workers revealed a contradictory structure. They had undertaken an X-ray an ...
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Patchouli
PatchouliAlso spelled ''patchouly'' or ''pachouli''. (; ''Pogostemon cablin'') is a species of flowering plant in the family Lamiaceae, commonly called the mint or deadnettle family. The plant grows as a bushy perennial herb, with erect stems reaching up to 75 centimetres (2.5 ft) in height and bearing small, pale pink-white flowers. It is native to the island region of Southeast Asia, including Sri Lanka, Indonesia, the Malay Peninsula, New Guinea and the Philippines. It is also found in many parts of North East India. Noted for its fragrant essential oil, it has many commercial uses and is now extensively cultivated in tropical climates around the world, especially in Asia, Madagascar, South America and the Caribbean. Indonesia currently produces over 90% of the global volume of patchouli oil (~1,600 metric tons). Etymology The word derives from the Tamil ''patchai'' ( ta, பச்சை) or paccuḷi, meaning "green", and ''ellai'' ( ta, இலை), meaning "leaf". ...
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Sesquiterpene
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids. Sesquiterpenes are found naturally in plants and insects, as semiochemicals, e.g. defensive agents or pheromones. Biosynthesis and examples The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate (FPP), which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Cyclic sesquiterpenes are more common than cyclic monoterpenes because of the increased chain length and additional double bond in the sesquiterpene precursors. In addition to common six-membered ring systems such as the ones found in zingiberene and bisacurone, cyclization of one end of the chain to the other end can ...
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Terpene
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene, is a major component of the common solvent, turpentine. History and terminology The term ''terpene'' was coined in 1866 by the German chemist August Kekulé to denote all hydrocarbons having the empirical formula C10H16, of which camphene was one. Previously, many hydrocarbons having the empirical formula C10H16 had been called "camphene", but many other hydrocarbons of the same composition had had different names. Kekulé coined the term "terpene" in order to reduce the confusion. The name "terpene" is a shortened form of "terpentine", an obsolete spelling of "turpentine". Although sometim ...
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Optical Isomer
In chemistry, a molecule or ion is called chiral () if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality (). The terms are derived from Ancient Greek χείρ (''cheir'') 'hand'; which is the canonical example of an object with this property. A chiral molecule or ion exists in two stereoisomers that are mirror images of each other, called enantiomers; they are often distinguished as either "right-handed" or "left-handed" by their absolute configuration or some other criterion. The two enantiomers have the same chemical properties, except when reacting with other chiral compounds. They also have the same physical properties, except that they often have opposite optical activities. A homogeneous mixture of the two enantiomers in equal parts is said to be racemic, and it usually differs chemically and physically from the pure enantiomers. Chiral molecules will u ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Liv ...
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Taxol
Paclitaxel (PTX), sold under the brand name Taxol among others, is a chemotherapy medication used to treat a number of types of cancer. This includes ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical cancer, and pancreatic cancer. It is administered by intravenous injection. There is also an albumin-bound formulation. Common side effects include hair loss, bone marrow suppression, numbness, allergic reactions, muscle pains, and diarrhea. Other serious side effects include heart problems, increased risk of infection, and lung inflammation. There are concerns that use during pregnancy may cause birth defects. Paclitaxel is in the taxane family of medications. It works by interference with the normal function of microtubules during cell division. Paclitaxel was first isolated in 1971 from the Pacific yew and approved for medical use in 1993. It is on the World Health Organization's List of Essential Medicines. It has been made f ...
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George Büchi
George Hermann Büchi (August 1, 1921 – August 28, 1998) was a Swiss organic chemist and professor at the Massachusetts Institute of Technology. "Paternò's reaction", known since the early twentieth century, was renamed to the "Paternò–Büchi reaction The Paternò–Büchi reaction, named after Emanuele Paternò and George Büchi, who established its basic utility and form, is a photochemical reaction, specifically a 2+2 photocycloaddition, which forms four-membered oxetane rings from an excit ..." based on enhancements made to it by Büchi's research group. Büchi died at the age of 77 of heart failure while hiking with his wife in Switzerland. References 1921 births 1998 deaths Organic chemists Massachusetts Institute of Technology faculty Members of the United States National Academy of Sciences Swiss expatriates in the United States {{chemist-stub ...
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Proposed Sequence Patchouli Alcohol
Proposal(s) or The Proposal may refer to: * Proposal (business) * Research proposal * Proposal (marriage) * Proposition, a proposal in logic and philosophy Arts, entertainment, and media * ''The Proposal'' (album) Films * ''The Proposal'' (1957 film), an Australian television play based on Chekhov's 1890 play * ''The Proposal'' (2001 film), starring Nick Moran, Jennifer Esposito, and Stephen Lang * ''The Proposal'' (2009 film), starring Sandra Bullock and Ryan Reynolds * ''The Proposal'' (2022 film), starring Joe Joseph and Amara Raja * " La propuesta" ("The Proposal"), a short story in the 2014 Argentina anthology film ''Wild Tales'' Literature * ''Proposals (play)'', a 1997 play by Neil Simon * ''The Proposal'' (novel), 1999 and 35th book in the ''Animorphs'' series by K.A. Applegate * ''The Proposal'', alternative title of Chekhov's 1890 play '' A Marriage Proposal'' Television * ''The Proposal'' (American TV series), a 2018 reality dating series * The Proposal (Au ...
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Jack D
Jack may refer to: Places * Jack, Alabama, US, an unincorporated community * Jack, Missouri, US, an unincorporated community * Jack County, Texas, a county in Texas, USA People and fictional characters * Jack (given name), a male given name, including a list of people and fictional characters with the name * Jack (surname), including a list of people with the surname * Jack (Tekken), multiple fictional characters in the fighting game series ''Tekken'' * Jack the Ripper, an unidentified British serial killer active in 1888 * Wolfman Jack (1938–1995), a stage name of American disk jockey Robert Weston Smith * New Jack, a stage name of Jerome Young (1963-2021), an American professional wrestler * Spring-heeled Jack, a creature in Victorian-era English folklore Animals and plants Fish *Carangidae generally, including: ** Almaco jack ** Amberjack **Bar jack **Black jack (fish) **Crevalle jack **Giant trevally or ronin jack **Jack mackerel ** Leather jack ** Yellow jack *Coho s ...
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X-ray Crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles and intensities of these diffracted beams, a crystallographer can produce a three-dimensional picture of the density of electrons within the crystal. From this electron density, the mean positions of the atoms in the crystal can be determined, as well as their chemical bonds, their crystallographic disorder, and various other information. Since many materials can form crystals—such as salts, metals, minerals, semiconductors, as well as various inorganic, organic, and biological molecules—X-ray crystallography has been fundamental in the development of many scientific fields. In its first decades of use, this method determined the size of atoms, the lengths and types of chemical bonds, and the atomic-scale differences among variou ...
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Chromic Acid
The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixture for glass. Chromic acid may also refer to the molecular species, H2CrO4 of which the trioxide is the anhydride. Chromic acid features chromium in an oxidation state of +6 (or VI). It is a strong and corrosive oxidising agent. Molecular chromic acid Molecular chromic acid, H2CrO4, has much in common with sulfuric acid, H2SO4. Only sulfuric acid can be classified as part of the 7 strong acids list. Due to the laws pertinent to the concept of "first order ionization energy", the first proton is lost most easily. It behaves extremely similar to sulfuric acid deprotonation. Since the process of polyvalent acid-base titrations have more than one proton (especially when the acid is starting substance and the base is the titrant), protons ...
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Peroxy Acid
A peroxy acid (often spelled as one word, peroxyacid, and sometimes called peracid) is an acid which contains an acidic –OOH group. The two main classes are those derived from conventional mineral acids, especially sulfuric acid, and the peroxy derivatives of organic carboxylic acids. They are generally strong oxidizers. Inorganic peroxy acids Peroxymonosulfuric acid (Caro's acid) is probably the most important inorganic peracid, at least in terms of its production scale. It is used for the bleaching of pulp and for the detoxification of cyanide in the mining industry. It is produced by treating sulfuric acid with hydrogen peroxide. Peroxymonophosphoric acid (H3PO5) is prepared similarly. Organic peracids Several organic peroxyacids are commercially useful. They can be prepared in several ways. Most commonly, peracids are generated by treating the corresponding carboxylic acid with hydrogen peroxide: :RCO2H + H2O2 RCO3H + H2O A related reaction involves treatm ...
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