Cyperotundone

Last updated
Cyperotundone
Cyperotundone.svg
Names
IUPAC name
(1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.01,5]undec-4-en-3-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C15H22O/c1-9-5-6-11-7-12-10(2)13(16)8-15(9,12)14(11,3)4/h9,11H,5-8H2,1-4H3/t9-,11-,15+/m1/s1
    Key: GIGKXOAUYMWORB-OSQNNJELSA-N
  • CC1(C)[C@]23C(C[C@H]1CC[C@H]2C)=C(C)C(=O)C3
Properties
C15H22O
Molar mass 218.340 g·mol−1
Melting point 46-47.5 °C
Boiling point 286.40 °C [1]
0.04497 g/L [1]
log P 6.570 [1]
Hazards
Flash point 114.50 °C [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyperotundone is an organic ketone with the formula C15H22O. It is found in many essential oils including that of Cyperus articulatus [2] [3] and Cyperus rotundus . [3] [4]

Related Research Articles

<span class="mw-page-title-main">Ketone bodies</span> Chemicals produced during fat metabolism

Ketone bodies are water-soluble molecules or compounds that contain the ketone groups produced from fatty acids by the liver (ketogenesis). Ketone bodies are readily transported into tissues outside the liver, where they are converted into acetyl-CoA —which then enters the citric acid cycle and is oxidized for energy. These liver-derived ketone groups include acetoacetic acid (acetoacetate), beta-hydroxybutyrate, and acetone, a spontaneous breakdown product of acetoacetate.

<span class="mw-page-title-main">Ketosis</span> Using body fats as fuel, not carbohydrates

Ketosis is a metabolic state characterized by elevated levels of ketone bodies in the blood or urine. Physiological ketosis is a normal response to low glucose availability, such as low-carbohydrate diets or fasting, that provides an additional energy source for the brain in the form of ketones. In physiological ketosis, ketones in the blood are elevated above baseline levels, but the body's acid–base homeostasis is maintained. This contrasts with ketoacidosis, an uncontrolled production of ketones that occurs in pathologic states and causes a metabolic acidosis, which is a medical emergency. Ketoacidosis is most commonly the result of complete insulin deficiency in type 1 diabetes or late-stage type 2 diabetes. Ketone levels can be measured in blood, urine or breath and are generally between 0.5 and 3.0 millimolar (mM) in physiological ketosis, while ketoacidosis may cause blood concentrations greater than 10 mM.

<span class="mw-page-title-main">Carbonyl group</span> Functional group (C=O)

In organic chemistry, a carbonyl group is a functional group with the formula C=O, composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.

<span class="mw-page-title-main">Cyperaceae</span> Family of flowering plants known as sedges

The Cyperaceae are a family of graminoid (grass-like), monocotyledonous flowering plants known as sedges. The family is large, with some 5,500 known species described in about 90 genera, the largest being the "true sedges" genus Carex with over 2,000 species.

<span class="mw-page-title-main">Hydrazone</span> Organic compounds - Hydrazones

Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.

<span class="mw-page-title-main">Vampire bat</span> Species of bat

Vampire bats, species of the subfamily Desmodontinae, are leaf-nosed bats found in Central and South America. Their food source is blood of other animals, a dietary trait called hematophagy. Three extant bat species feed solely on blood: the common vampire bat, the hairy-legged vampire bat, and the white-winged vampire bat. All three species are native to the Americas, ranging from Mexico to Brazil, Chile, Uruguay and Argentina.

<i>Cyperus</i> Genus of plants

Cyperus is a large genus of about 700 species of sedges, distributed throughout all continents in both tropical and temperate regions.

<i>Cyperus esculentus</i> Species of grass-like plant

Cyperus esculentus is a species of plant in the sedge family widespread across much of the world. It is found in most of the Eastern Hemisphere, including Southern Europe, Africa and Madagascar, as well as the Middle East and the Indian subcontinent. C. esculentus is cultivated for its edible tubers, called earth almonds or tiger nuts, as a snack food and for the preparation of horchata de chufa, a sweet, milk-like beverage.

<span class="mw-page-title-main">Eucalyptol</span> 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 ~70% - 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.

<i>Cyperus rotundus</i> Species of plant

Cyperus rotundus is a species of sedge (Cyperaceae) native to Africa, southern and central Europe, and southern Asia. The word cyperus derives from the Greek κύπερος, kyperos, and rotundus is from Latin, meaning "round". The earliest attested form of the word cyperus is the Mycenaean Greek 𐀓𐀞𐀫, ku-pa-ro, written in Linear B syllabic script.

Trifluoroiodomethane, also referred to as trifluoromethyl iodide is a halomethane with the formula CF3I. It is an experimental alternative to Halon 1301 (CBrF3) in unoccupied areas. It would be used as a gaseous fire suppression flooding agent for in-flight aircraft and electronic equipment fires.

<i>Cyperus articulatus</i> Species of plant in Cyperaceae family

Cyperus articulatus is an aromatic species of sedge known by the common names jointed flatsedge and priprioca. It has also been known as Guinea rush or adrue. It grows as a perennial herb. It grows in water or near it in rivers, streams, lakes, and swamps with a hyperhydrate or possibly tenagophyte growth pattern. It is widespread across tropical and subtropical regions in Africa, southern Asia, northern Australia, the southeastern United States, the West Indies, and Latin America. While it is closely related to highly invasive sedges such as purple nut sedge, priprioca is less prolific and competitive than its relative.

α-Cadinol Chemical compound

α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol.

<span class="mw-page-title-main">Rotundone</span> Chemical compound

Rotundone is a sesquiterpene originally discovered in the tubers of Java grass. Rotundone is also present in the essential oils of black pepper, marjoram, oregano, rosemary, basil, thyme, and geranium, as well as in some Syrah wines. It imparts a peppery aroma.

<span class="mw-page-title-main">Curzerene</span> Chemical compound

Curzerene is a volatile, aromatic terpenoid found in many herbs and spices, such as Curcuma zeodaria. It is bioactive isolate of Caribbean corals and is also found in myrrh. More specifically it has been found to make up a significant portion - 12.97% - of the smoke produced from burning Commiphora myrrha oleo gum resin. It is also a major component of myrrh oil, which has been shown in vitro to possess anti-inflammatory properties at sub-toxic by inhibiting the production of the inflammatory cytokine IL-6 by human gingival fibroblasts. Anecdotal evidence exists to support the anti-inflammatory effect of myrrh oil.

<span class="mw-page-title-main">Ledol</span> Chemical compound

Ledol is a poisonous sesquiterpene that can cause cramps, paralysis, and delirium. Caucasian peasants used Rhododendron plants for these effects in shamanistic rituals.

<span class="mw-page-title-main">2,4,5-Trihydroxycinnamic acid</span> Chemical compound

2,4,5-Trihydroxycinnamic acid is a hydroxycinnamic acid found in rooibos tea. cis-2,4,5-Trihydroxycinnamic acid can be isolated from seeds of Alisma orientale.

<span class="mw-page-title-main">Bornyl acetate</span> Chemical compound

Bornyl acetate is a chemical compound. Its molecular formula is C12H20O2 and its molecular weight is 196.29 g/mol. It is the acetate ester of borneol. It is used as a food additive, flavouring agent, and odour agent.

<span class="mw-page-title-main">Pinocarveol</span> Chemical compound Pinocarveol

Pinocarveol is an organic compound with the formula C10H16O. It is a bicyclic monoterpenoid, which is a combination of two isoprene units with one hydroxyl group as a substituent. It exists as either trans- or cis-pinocarveol, referring to stereochemical orientation of the oxygen as compared to the methylene bridge. It is a naturally occurring molecule in numerous plant species including Eucalyptus globulus and Picea abies. Pinocarveol is found in a variety of essential oils.

<span class="mw-page-title-main">Mustakone</span> Chemical compound

Mustakone is a tricylic sesquiterpenoid with the chemical formula C15H22O. It is named after the plant it was first extracted from Cyperus rotundus, which had the common name "mustuka" in Hindi. Mustakone can be found in a variety of plants and their oils like Myrcia sylvatica, Cyperus articulatus, and Hymenaea courbaril.

References

  1. 1 2 3 4 "cyperotundone, 3466-15-7". www.thegoodscentscompany.com. Retrieved 2022-08-10.
  2. Azambuja, Wagner. "Priprioca Essential Oil - Óleos Essenciais O Guia do Brasil". Óleos Essenciais. Brazil. Archived from the original on 13 September 2017. Retrieved 12 September 2017.
  3. 1 2 Hikino, H.; Aota, K.; Takemoto, T. (May 1967). "Identification of ketones inCyperus". Tetrahedron. 23 (5): 2169–2172. doi:10.1016/0040-4020(67)80050-4. PMID   6044197.
  4. Wang, Qiang; Yi, Chundie; Duan, Wenlan; Duan, Yunfeng; Lou, Jiahao; Zeng, Guangzhi; Yin, Junlin (February 2021). "Two New Sesquiterpenoids Isolated From Cyperus rotundus L". Natural Product Communications. 16 (2): 1934578X2199168. doi: 10.1177/1934578X21991687 . ISSN   1934-578X.