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Rosmarinic acid

Rosmarinic acid is a natural antioxidant with strong antioxidant activity, which is stronger than vitamin E, caffeic acid, chlorogenic acid, folic acid and helps to prevent cell damage caused by free radicals, thus reducing the risk of cancer and atherosclerosis.Rosmarinic acid has strong anti-inflammatory activity, as well as anti-bacterial, anti-viral, anti-tumor activity, and the characteristics in inhibiting acute and chronic infection, anti-ultraviolet, inhibiting elastin degradation have made rosmarinic acid cosmetic additives. Currently, rosmarinic acid has showed its important applications in the pharmaceutical, food, cosmetics and other fields.
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Products Intro: Product Name:Rosmarinic acid
CAS:20283-92-5
Purity:HPLC>=98% Package:20mg
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CAS:20283-92-5
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Products Intro: Product Name:RosMarinic acid
CAS:20283-92-5
Purity:98%以上,HPLC Package:20Mg;100Mg;g;5g
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Products Intro: Product Name:RosMarinic acid
CAS:20283-92-5
Purity:98% Package:5G
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Products Intro: Product Name:RosMarinic acid;[R-(+)]-α-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxybenzenepropanoicacid
CAS:20283-92-5
Purity:99% HPLC Package:1Mg ; 5Mg;10Mg ;100Mg;250Mg ;500Mg ;1g;2.5g ;5g ;10g
Rosmarinic acid Basic information
Plant extracts Rosmarinus officinalis Antibacterial effects Antioxidant Effects Antidepressant Effects Stability
Product Name:Rosmarinic acid
Synonyms:3-(3,4-DIHYDROXYPHENYL)ACRYLIC ACID-1-CARBOXY-2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER;3,4-DIHYDROXYCINNAMIC ACID (R)-1-CARBOXY-2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER;[4ar-(4aa,9b,10a,10ab)]-1,3,4,9,10,10a-hexahydro-5,6,9-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2h-10,4a-(epoxymethano)phenanthren-12-one;ROSMARINATE;(r)-o-(3,4-dihydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)lactic acid;(R)-2-(3,4-DIHYDROXYCINNAMOYLOXY)-3-(3,4-DIHYDROXYPHENYL)LACTIC ACID;(R)-ALPHA-[[3-(3,4-DIHYDROXYPHENYL)-1-OXO-2E-PROPENYL]OXY]-3,4-DIHYDROXY-BENZENEPROPANOIC ACID;[R-(+)]-ALPHA-[[3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL]OXY]-3,4-DIHYDROXYBENZENEPROPANOIC ACID
CAS:20283-92-5
MF:C18H16O8
MW:360.31
EINECS:
Product Categories:Plant Oils, Toxins, Phenolic Acids & Derivatives;Prostanoid receptor and related;Plant extracts;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Lignans
Mol File:20283-92-5.mol
Rosmarinic acid Structure
Rosmarinic acid Chemical Properties
mp 171-175 °C(lit.)
density 1.33
storage temp. Store at RT
CAS DataBase Reference20283-92-5(CAS DataBase Reference)
Safety Information
Hazard Codes T
Risk Statements 25
Safety Statements 45
WGK Germany 3
RTECS GD8990000
10-23
MSDS Information
ProviderLanguage
SigmaAldrich English
Rosmarinic acid Usage And Synthesis
Plant extracts Rosmarinic acid is a water-soluble natural phenolic acid compound that extracted from Rosmarinus officinalis (Lamiaceae), with a wide distribution. It mainly exists in a variety of plants in Lamiaceae, Boraginaceae, Cucurbitaceae, Tiliaceae, and Umbelliferae, especially with the highest content in Lamiaceae and Boraginaceae.
Rosmarinic acid is a natural antioxidant with strong antioxidant activity, which is stronger than vitamin E, caffeic acid, chlorogenic acid, folic acid and helps to prevent cell damage caused by free radicals, thus reducing the risk of cancer and atherosclerosis.
Rosmarinic acid has strong anti-inflammatory activity, as well as anti-bacterial, anti-viral, anti-tumor activity, and the characteristics in inhibiting acute and chronic infection, anti-ultraviolet, inhibiting elastin degradation have made rosmarinic acid cosmetic additives. Currently, rosmarinic acid has showed its important applications in the pharmaceutical, food, cosmetics and other fields.
In summary, rosmarinic acid has very broad application prospects and market value, with the main application areas are:
1. The food industry: as a natural high antioxidant, rosmarinic acid can replace BHA, BHT to be used in animal and plant fats, dairy products, oil-rich food, candy and baked food; and it is also used as a spice for a variety of soups and flavoring foods, with both antiseptic and antibacterial effects. In Japan, rosmarinic acid-rich perillae extracts is used as garnish to improve the expiration date of fresh seafood.
2. The field of health care products: it has effects in anti-tumor, anti-hepatitis and protecting liver injury, anti-nephritis, anti-thrombotic and anti-platelet aggregation, as well as refreshing, enhancing memory, improving tension and lethargy.
3. Cosmetic field: when used in skin care products, it can play a role in removing stains, anti-oxidation, increasing skin elasticity, anti-aging; when used in shampoo and hair care products, it can promote scalp blood circulation, improve hair loss, reduce occurrence of dandruff, stimulate hair growth, moist and nourish hairs. Therefore, rosmarinic acid can be an excellent additive in cosmetics.
Rosmarinus officinalisRosmarinus officinalis belongs to genus Rosmarinus and family Lamiaceae. This plant is a small evergreen shrub, about 1 meter high, and young shoots are 4-sided and closely arranged, with dense hairs; leaves opposite, sessile, leathery, linear, with surface dark green and smooth, and leaf back gray and finely hairy; Flowers bisexual, paired grown on short stalk, axillary, calyx bell-shaped, two lips, with upper lip entire and lower lip two-lobed; corolla 3 times longer than calyx, 2 lips, with upper lip furrow into two-lobs and lower lip concavely tri-lobed to the middle; 2 fertile stamens that extend out of the flower; flowers pale blue color, sometimes pink or white; flowers in spring, with a rich aroma.
Rosmarinus officinalis is native to the North Africa and was transported to China after Zhang Qian went to the Western Regions, and it was a traditional commodity among Roman Empire, the Eastern Roman Empire and China, that’s why Chinese also called it "the Daqin aroma."
This plant is both a medicinal and edible herb with an oil body, and it is available for viewing and extracting aroma, and the fresh twigs and buds of rosemary can be used also to extract aromatic oils. This aromatic oil is used in deployment of food flavor and seasoners and the production of sauce. As a food seasoner, Rosmarinus officinalis is seldom used in Chinese food but mainly in western food, it is quite common in Europe, and is still a very popular cooking spice in Europe so far.
The Photo of Rosmarinus officinalis
Figure 1 The Photo of Rosmarinus officinalis
Rosmarinus officinalis is a historic spice plant, which is native to the Mediterranean coast. It was first introduced to China in 1981 by the Chinese Academy of Sciences and with the successful cultivation, and now has been grown in Yunnan, Hunan, Sichuan, Guizhou, Guangxi and other places. Rosmarinus officinalis is a valuable natural aromatic plant, and in the growing season it will emit a kind of fragrance smell with the function of purifying heart and refreshing spirits. Its stems, leaves and flowers have a pleasant scent, and aromatic oil that extracted from flowers and twigs can be used to deploy air cleaners, perfumes, soaps and other cosmetics. The most famous lotion is made with rosemary, and it can be used in beverages, skin care oils, hair tonic, washing paste. As a medicine, it can be used in treatment of neurological disorders and in ointment production to treat headache and rheumatism. In recent years, it has also been found to be an ideal natural preservative. It also can be planted or potted as ornamental plants.
Rosmarinus officinalis is a versatile commercial crop, from which antioxidants and rosemary essential oils and pharmaceutical intermediates can be extracted.
Antioxidants are powdery substance that extracted from Rosmarinus officinalis; with the main ingredients with antioxidant function are phenolic, acids, and flavonoids and so on.
rosemary essence oil is a kind of liquid oil consisting of 30 kinds of volatile components.
The powdery extract substance rosmarinic acid from Rosmarinus officinalis has an efficient, non-toxic antioxidant effect and can be widely used in food, functional foods, spices and condiments and household chemicals industries.
Antibacterial effectsRosmarinic acid has a broad-spectrum anti-microbial activity against bacteria and fungi. Rosmarinic acid can significantly inhibit Bacillus subtilis, Micrococcus luteus, Escherichia coli, Staphylococcus aureus and Rhizoctonia and other bacteria. Neusa found that rosmarinic acid could inhibit the growth of Streptococcus mutans and Caries streptococci and the formation of biological membrane, reducing their glucose transferase activity, which indicating that rosmarinic acid can be used for oral disease prevention and treatment. Studies in mechanism of antibacterial activity of rosmarinic acid showed: on the one hand, rosmarinic acid can increase the permeability of the bacterial cell membrane, resulting in a lot of leakage of carbohydrates and protein, affecting the normal metabolism of bacteria; on the other hand, it can also affect protein metabolism of bacteria, and also inhibit Taq DNA polymerase.
Guo Daosen studied the inhibition effects of rosmarinic acid on mycelial growth and spore germination of different plant pathogenic fungi, and found that rosmarinic acid had stronger inhibition on mycelial growth of tomato Botrytis cinerea, mango gray leaf spot pathogen, citrus Penicillium and pear Alternaria panax, with the strongest inhibition in spore germination of pear Alternaria panax.
Rosmarinic acid has antibacterial activity on both the Gram-negative bacteria E. coli and the Gram-positive bacteria Staphylococcus aureus, but the sensitivity of S. aureus to rosmarinic acid is significantly higher than that of E. coli. The results also show that rosmarinic acid can significantly increase the permeability of the bacterial cell membrane, accelerate the leakage of carbohydrate and protein, and cause disorder of the cell metabolism. Rosmarinic acid can affect protein metabolism of bacteria. By comparing the total protein in Staphylococcus aureus before and after the treatment of rosmarinic acid, it is known that treatment of rosmarinic acid promotes degradation of certain proteins in bacterial metabolism, or promotes the synthesis of certain proteins in short term. As for which specific protein is affected by rosmarinic acid, further identification is still needed. Through the experimental results of interaction between rosmarinic acid and plasmid DNA, we know that rosmarinic acid does not interact with DNA, whereby it can be speculated that rosmarinic acid can not bind with the primers in the polymerase chain reaction system, thus rosmarinic acid inhibits polymerization chain reaction because this compound inhibits the binding activity of the DNA polymerase, thereby inhibiting the replication of DNA. In summary, rosmarinic acid has a certain influence on the permeability of cell membrane, protein metabolism and DNA replication in bacteria, and thus plays its anti-bacteria effect.
The above information is edited by the Chemicalbook of Cheng Jingmin.
Antioxidant EffectsRosmarinic acid has a strong activity in scavenging free radicals in body and antioxidant. Studies show that the mechanism is: rosmarinic acid competes with unsaturated fatty acids to bind with lipid peroxy to terminate the chain reaction of lipid peroxidation and reduce lipid peroxidation rate, with rosmarinic acid being oxidized to quinone; Rosmarinic acid inhibits neutrophil respiratory burst and release of lysosomes by reducing the concentration of intracellular calcium ion; and it can inhibit the endothelial cell-mediated oxidation of LDL.
The antioxidant effect of rosmarinic acid is related to its structure, and Nakamura et al. think that adjacent phenolic hydroxyl groups are the material basis of the activity in scavenging free radical, and C3 conjugated double bonds have a synergistic effect.
Antidepressant EffectsRosmarinic acid has antidepressant effect on depression model for animal. ItoN et al. performed experiments on cell proliferation in mouse brain hippocampus and immunohistochemical analysis by using the antibody BrdU to explore the mechanism, and they found increased number of marked proliferated cells in the rosmarinic acid treatment group. Combined with the forced swim test of depression model for animal, it showed that rosmarinic acid produces an antidepressant-like effect at least in part by the proliferation of new cells in the hippocampus.
StabilityStudy results on stability of rosmarinic acid showed that rosmarinic acid has good stability. Salt and sugar have no effect on stability of rosmarinic acid. pH and temperature have small effect on stability of rosmarinic acid, and the results show that rosmarinic acid is more suitable to use and store in an acidic and low temperatures; Light has great impact on rosmarinic acid, thus it should be used as much as possible in the dark. Ca2 + and Mg2 + have great impact on the stability of rosmarinic acid, but other metal ions have less impact on the stability of rosmarinic acid, thus it should be used without contacting with calcium and magnesium as much as possible. Low concentration of sodium benzoate and potassium sorbate have small effect on stability of rosmarinic acid, thus their application in food should be appropriate, in accordance with the sanitary standards for food additives. Ascorbic acid has certain impact on the rosmarinic acid, with the less effect in lower concentration. The oxidizing agent hydrogen peroxide has large impact on rosmarinic acid; but the reducing agent sodium metabisulfite has small impact on rosmarinic acid.
Chemical PropertiesWhite to off-white powder
UsageRosmarinic Acid is a phenolic compound with antioxidant and anti-inflammatory activity. Rosmarinic Acid has been shown to inhibit againts peroxidative damage to biomembranes. Rosmarinic Acid also supp resses endotoxin-induced activation of complement and concomitant prostacyclin biosynthesis.
Biological ActivityAnti-inflammatory, cytostatic and antiviral.
Rosmarinic acid Preparation Products And Raw materials
Tag:Rosmarinic acid(20283-92-5) Related Product Information
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