Sclareolide

Last updated
Sclareolide
Sclareolide.svg
Names
IUPAC name
3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[8,7-d]furan-2-one
Other names
Norambreinolide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.427 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-269-0
PubChem CID
UNII
  • InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1 X mark.svgN
    Key: IMKJGXCIJJXALX-SHUKQUCYSA-N X mark.svgN
  • InChI=1/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1
    Key: IMKJGXCIJJXALX-SHUKQUCYBO
  • C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CC(=O)O3)C)(C)C
Properties
C16H26O2
Molar mass 250.382 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sclareolide is a sesquiterpene lactone natural product derived from various plant sources including Salvia sclarea , Salvia yosgadensis , [1] and cigar tobacco. [2] It is a close analog of sclareol, a plant antifungal compound. [3]

It is used as a fragrance in cosmetics [4] and has been more recently marketed as a weight loss supplement, though there is no clinical evidence to support this effect.

Related Research Articles

<span class="mw-page-title-main">Rosemary</span> Species of plant

Salvia rosmarinus, commonly known as rosemary, is a shrub with fragrant, evergreen, needle-like leaves and white, pink, purple, or blue flowers, native to the Mediterranean region. Until 2017, it was known by the scientific name Rosmarinus officinalis, now a synonym.

<span class="mw-page-title-main">Tobacco</span> Agricultural product processed from the leaves of plants in the genus nicotiana

Tobacco is the common name of several plants in the genus Nicotiana of the family Solanaceae, and the general term for any product prepared from the cured leaves of these plants. More than 70 species of tobacco are known, but the chief commercial crop is N. tabacum. The more potent variant N. rustica is also used in some countries.

<span class="mw-page-title-main">Cigar</span> Rolled bundle of dried and fermented tobacco leaves made to be smoked

A cigar is a tobacco product made to be smoked. Cigars are produced in a variety of shapes and sizes. Since the 20th century, almost all cigars are made of three distinct components: the filler, the binder leaf which holds the filler together, and a wrapper leaf, for appearance and flavor, which is often the highest quality leaf used. Often there will be a cigar band printed with the cigar manufacturer's logo. Modern cigars can come with two or more, highlighting special qualities such as age and origin of the tobaccos used.

<span class="mw-page-title-main">Cigarette</span> Small roll of cut tobacco designed to be smoked

A cigarette is a narrow cylinder containing a combustible material, typically tobacco, that is rolled into thin paper for smoking. The cigarette is ignited at one end, causing it to smolder; the resulting smoke is orally inhaled via the opposite end. Cigarette smoking is the most common method of tobacco consumption. The term cigarette, as commonly used, refers to a tobacco cigarette, but the word is sometimes used to refer to other substances, such as a cannabis cigarette or an herbal cigarette. A cigarette is distinguished from a cigar by its usually smaller size, use of processed leaf, and paper wrapping, which is typically white. Most modern cigarettes are filtered, although this does not make the smoke inhaled from them contain fewer carcinogens and harmful chemicals.

<span class="mw-page-title-main">Tobacco smoking</span> Practice of burning tobacco and breathing the resulting smoke

Tobacco smoking is the practice of burning tobacco and ingesting the resulting smoke. The smoke may be inhaled, as is done with cigarettes, or simply released from the mouth, as is generally done with pipes and cigars. The practice is believed to have begun as early as 5000–3000 BC in Mesoamerica and South America. Tobacco was introduced to Eurasia in the late 17th century by European colonists, where it followed common trade routes. The practice encountered criticism from its first import into the Western world onwards but embedded itself in certain strata of a number of societies before becoming widespread upon the introduction of automated cigarette-rolling apparatus.

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

Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.

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

Cinnamaldehyde is an organic compound with the formula or C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

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Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent. A colorless oil, linalool is classified as an acyclic monoterpenoid. In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate.

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Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the volatile oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common (-)-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

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

Eucalyptol is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 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.

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

Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from Myrcia, from which it gets its name. It is an intermediate in the production of several fragrances. α-Myrcene is the name for the isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature.

<i>Nicotiana tabacum</i> Species of plant

Nicotiana tabacum, or cultivated tobacco, is an annually grown herbaceous plant of the genus Nicotiana. N. tabacum is the most commonly grown species in the genus Nicotiana, as the plant's leaves are commercially harvested to be processed into tobacco for human use. The plant is tropical in origin, is commonly grown throughout the world, and is often found in cultivation. It grows to heights between 1 and 2 meters. Research is ongoing into its ancestry among wild Nicotiana species, but it is believed to be a hybrid of Nicotiana sylvestris, N. tomentosiformis, and possibly N. otophora.

<i>Salvia miltiorrhiza</i> Species of flowering plant

Salvia miltiorrhiza, also known as red sage, redroot sage, Chinese sage, or danshen, is a perennial plant in the genus Salvia, highly valued for its roots in traditional Chinese medicine. Native to China and Japan, it grows at 90 to 1,200 m elevation, preferring grassy places in forests, hillsides, and along stream banks. The specific epithet miltiorrhiza means "red ochre root".

<span class="mw-page-title-main">Bornyl diphosphate synthase</span>

In enzymology, bornyl diphosphate synthase (BPPS) (EC 5.5.1.8) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Flavored tobacco</span> Tobacco product with added flavorings

Flavored tobacco products — tobacco products with added flavorings — include types of cigarettes, cigarillos and cigars, hookahs and hookah tobacco, various types of smokeless tobacco, and more recently electronic cigarettes. Flavored tobacco products are especially popular with youth and have therefore become targets of regulation in several countries.

<i>Salvia divinorum</i> Species of plant

Salvia divinorum is a plant species with transient psychoactive properties when its leaves, or extracts made from the leaves, are administered by smoking, chewing, or drinking. The leaves contain the potent compound salvinorin A and can induce a dissociative state and hallucinations.

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

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum, Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

α-Cadinol Chemical compound

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

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

Acetyleugenol is a phenylpropanoid compound found in cloves. It is the second in abundance to the related compound eugenol in certain extract preparations. Like eugenol, its found in several plants such as Acacia nilotica and Piper betle and has similar antibacterial and antifungal properties on C. albicans and S. mutans. It inhibits aggregation of platelets and has partial agonistic activity on AhR.

References

  1. Topcu, Guelacti; Ulubelen, Ayhan; Tam, Timothy Chit-Ming; Che, Chun-Tao (1996). "Norditerpenes and Norsesterterpenes from Salvia yosgadensis". Journal of Natural Products . 59 (2): 113–116. doi:10.1021/np960028h.
  2. Kaneko, Hajime (1971). "Aroma of cigar tobacco. II. Isolation of norambreinolide from cigar tobacco". Agricultural and Biological Chemistry. 35 (9): 1461–1462. doi:10.1080/00021369.1971.10860098. S2CID   82467628.
  3. Jasiński M; Stukkens Y; Degand H; Purnelle B; Marchand-Brynaert J; Boutry M (2001). "A Plant Plasma Membrane ATP Binding Cassette–Type Transporter Is Involved in Antifungal Terpenoid Secretion". Plant Cell. 13 (5): 1095–107. doi:10.1105/tpc.13.5.1095. PMC   135550 . PMID   11340184.
  4. Api, A.M.; et al. (2022). "RIFM fragrance ingredient safety assessment, sclareolide, CAS Registry Number 564-20-5". Food and Chemical Toxicology. 167: 113379. doi:10.1016/j.fct.2022.113379. PMID   35995076. S2CID   251696291.