Names | |
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Preferred IUPAC name (2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.123.507 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C18H16O8 | |
Molar mass | 360.318 g·mol−1 |
Appearance | Red-orange powder |
Melting point | 171 to 175 °C (340 to 347 °F; 444 to 448 K) |
Slightly soluble | |
Solubility in other solvents | Well soluble in most organic solvents [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Rosmarinic acid, named after rosemary (Salvia rosmarinus Spenn.), is a polyphenol constituent of many culinary herbs, including rosemary (Salvia rosmarinus L.), perilla (Perilla frutescens L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). [1]
Rosmarinic acid was first isolated and characterized in 1958 by the Italian chemists Scarpatti and Oriente from rosemary ( Salvia rosmarinus ), [2] after which the acid is named.
Chemically, rosmarinic acid is a caffeic acid ester, with tyrosine providing another phenolic ring via dihydroxyphenyl-lactic acid. [1] It has a molecular mass of 360 daltons. [1]
Rosmarinic acid accumulation is shown in hornworts, in the fern family Blechnaceae, and in species of several orders of mono- and dicotyledonous angiosperms. [3]
It is found most notably in many Lamiaceae (dicotyledons in the order Lamiales), especially in the subfamily Nepetoideae. [1] [4] It is found in species used commonly as culinary herbs such as Ocimum basilicum (basil), Ocimum tenuiflorum (holy basil), Melissa officinalis (lemon balm), Salvia rosmarinus (rosemary), Origanum majorana (marjoram), Salvia officinalis (sage), thyme and peppermint. [1] [5] It is also found in plants in the family Marantaceae (monocotyledons in the order Zingiberales) [3] such as species in the genera Maranta ( Maranta leuconeura , Maranta depressa ) and Thalia ( Thalia geniculata ). [6]
Rosmarinic acid and the derivative rosmarinic acid 3′-O-β-D-glucoside can be found in Anthoceros agrestis , a hornwort (Anthocerotophyta). [7]
The biosynthesis of rosmarinic acid uses 4-coumaroyl-CoA from the general phenylpropanoid pathway as a hydroxycinnamoyl donor. [1] The hydroxycinnamoyl acceptor substrate comes from the shikimate pathway: shikimic acid, quinic acid and 3,4-dihydroxyphenyllactic acid derived from L-tyrosine. [3] Thus, chemically, rosmarinic acid is an ester of caffeic acid with 3,4-dihydroxyphenyllactic acid, but biologically, it is formed from 4-coumaroyl-4′-hydroxyphenyllactate. [8] Rosmarinate synthase is an enzyme that uses caffeoyl-CoA and 3,4-dihydroxyphenyllactic acid to produce CoA and rosmarinate. Hydroxyphenylpyruvate reductase is also an enzyme involved in this biosynthesis. [9]
When extracted from plant sources or synthesized in manufacturing, rosmarinic acid may be used in foods or beverages as a flavoring, in cosmetics, or as a dietary supplement. [1]
The Lamiaceae or Labiatae are a family of flowering plants commonly known as the mint, deadnettle, or sage family. Many of the plants are aromatic in all parts and include widely used culinary herbs like basil, mint, rosemary, sage, savory, marjoram, oregano, hyssop, thyme, lavender, and perilla, as well as other medicinal herbs such as catnip, salvia, bee balm, wild dagga, and oriental motherwort. Some species are shrubs, trees, or, rarely, vines. Many members of the family are widely cultivated, not only for their aromatic qualities, but also their ease of cultivation, since they are readily propagated by stem cuttings. Besides those grown for their edible leaves, some are grown for decorative foliage. Others are grown for seed, such as Salvia hispanica (chia), or for their edible tubers, such as Plectranthus edulis, Plectranthus esculentus, Plectranthus rotundifolius, and Stachys affinis. Many are also grown ornamentally, notably coleus, Plectranthus, and many Salvia species and hybrids.
Salvia rosmarinus, commonly known as rosemary, is a shrub with fragrant, evergreen, needle-like leaves and white, pink, purple, or blue flowers. It is native to the Mediterranean region, as well as Portugal and northwestern Spain. Until 2017, it was known by the scientific name Rosmarinus officinalis, now a synonym.
Thyme is a culinary herb consisting of the dried aerial parts of some members of the genus Thymus of flowering plants in the mint family Lamiaceae. Thymes are native to Eurasia and north Africa. Thymes have culinary, medicinal, and ornamental uses. The species most commonly cultivated and used for culinary purposes is Thymus vulgaris, native to Southeast Europe.
Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.
An insect repellent is a substance applied to the skin, clothing, or other surfaces to discourage insects from landing or climbing on that surface. Insect repellents help prevent and control the outbreak of insect-borne diseases such as malaria, Lyme disease, dengue fever, bubonic plague, river blindness, and West Nile fever. Pest animals commonly serving as vectors for disease include insects such as flea, fly, and mosquito; and ticks (arachnids).
Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term chlorogenic acids refers to a related polyphenol family of esters, including hydroxycinnamic acids with quinic acid.
Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine.
Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.
Edible flowers are flowers that can be consumed safely. Flowers may be eaten as vegetables as a main part of a meal, or may be used as herbs. Flowers are part of many regional cuisines, including Asian, European, and Middle Eastern cuisines.
In enzymology, a rosmarinate synthase is an enzyme that catalyzes the chemical reaction
In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.
Anthoceros agrestis, commonly called field hornwort, is a bryophyte of the family Anthocerotaceae.
The following outline is provided as an overview of and topical guide to herbs and spices:
p-Coumaroylated anthocyanins are a type of anthocyanins with a p-coumaric acid unit linked with a sugar to an anthocyanidin aglycone. 3-(6-p-Coumaroyl)glucosides are found in grape and wine. Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside is found in dark opal basil. Red leaves of Perilla frutescens also accumulate cyanidin 3-(6-O-p-coumaroyl-β-D-glucoside)-5-(6-O-malonyl-β-D-glucoside).
Maranta leuconeura, widely known as the prayer plant due to its daily sunlight-dependent movements, is a species of flowering plant in the family Marantaceae native to the Brazilian tropical forests. It is a variable, rhizomatous perennial, growing to 30 cm (12 in) tall and broad, with crowded clumps of evergreen, strikingly-marked oval leaves, each up to 12 cm (5 in) long. The plant spreads itself horizontally, carpeting an entire small area of forest floor, sending roots into the substrate at each leaf node.
The history of spices reach back thousands of years, dating back to the 8th century B.C. Spices are widely known to be developed and discovered in Asian civilizations. Spices have been used in a variety of antique developments for their unique qualities. There were a variety of spices that were used for common purposes across the ancient world. Different spices hold a value that can create a variety of products designed to enhance or suppress certain taste and/or sensations. Spices were also associated with certain rituals to perpetuate a superstition or fulfill a religious obligation, among other things.
In biochemistry, the direct linear plot is a graphical method for enzyme kinetics data following the Michaelis–Menten equation. In this plot, observations are not plotted as points, but as lines in parameter space with axes and , such that each observation of a rate at substrate concentration is represented by a straight line with intercept on the axis and on the axis. Ideally the lines intersect at a unique point whose coordinates provide the values of and .