Rosmarinic
Rosmarinic acid
CAS: 20283-92-5;537-15-5
Molecular Formula: C18H16O8
Rosmarinic - Names and Identifiers
| Name | Rosmarinic acid |
| Synonyms | Rosmarinic rosemaryacid Rosmarinic acid Rosemarinic acid ROSMARINIC ACID(P) r-(+)-2-(3,4-dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionicacid 3-(3,4-DIHYDROXYPHENYL)ACRYLIC ACID-1-CARBOXY-2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER 3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid (R)-alpha-[3-(3,4-Dihydroxyphenyl)-1-oxo-2E-propenyl]oxy-3,4-dihydroxybenzenepropanoic acid (2S)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid |
| CAS | 20283-92-5 537-15-5 |
| EINECS | 606-487-1 |
| InChI | InChI=1/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+ |
| InChIKey | DOUMFZQKYFQNTF-WUTVXBCWSA-N |
Rosmarinic - Physico-chemical Properties
| Molecular Formula | C18H16O8 |
| Molar Mass | 360.31 |
| Density | 1.33 |
| Melting Point | 171-175 °C (lit.) |
| Boling Point | 694.7±55.0 °C(Predicted) |
| Specific Rotation(α) | +102～+110°(D/20℃)(c=0.2,C2H5OH) |
| Flash Point | 254.5°C |
| Solubility | Insoluble in petroleum ether, soluble in methanol, soluble in ethyl acetate under hot conditions. |
| Vapor Presure | 2.92E-20mmHg at 25°C |
| Appearance | White to Brown Powder |
| Color | white to faintly beige |
| BRN | 2227587 |
| pKa | 2.78±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. |
| Sensitive | Sensitive to air |
| Refractive Index | 1.713 |
| MDL | MFCD00017740 |
| Physical and Chemical Properties |
Rosmarinic - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | 25 - Toxic if swallowed |
| Safety Description | 45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | GD8990000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29189900 |
Rosmarinic - Reference Information
| Plant source: | Rosemary |
| plant extract | rosmarinic acid is a water-soluble natural phenolic acid compound isolated from the labiatae plant rosemary. It is widely distributed and mainly exists in many plants in the Labiatae, Araginaceae, Cucurbitaceae, Linden and Umbelliferae, especially in the Labiatae and Araginaceae. Rosmarinic acid is a natural antioxidant with strong antioxidant activity. Its antioxidant activity is stronger than vitamin E, caffeic acid, chlorogenic acid, folic acid, etc., which helps prevent cell damage caused by free radicals, thus reducing the risk of cancer and arteriosclerosis. rosmarinic acid has strong anti-inflammatory activity, and rosmarinic acid also has antibacterial, antiviral and anti-tumor activities, and has the characteristics of inhibiting acute and chronic infection, anti-ultraviolet rays, and inhibiting elastin degradation. Rosmarinic acid has become an additive for cosmetics. At present, rosmarinic acid has shown its important application value in pharmaceutical, food, cosmetics and other fields. In summary, the rosmarinic acid has very broad application prospects and market value. The main application fields: 1. Food field: rosmarinic acid is a natural and efficient antioxidant, which can replace BHA and BHT in animal and vegetable fats, dairy products, oil-rich foods, candies and baked foods; it can also be used as a spice in various soups and flavored foods; it also has antiseptic and antibacterial effects. In Japan, perilla extract rich in rosmarinic acid is used as a decoration to improve the shelf life of fresh seafood. 2. The field of health products: anti-tumor, anti-hepatitis and protection of liver injury, anti-nephritis, anti-thrombosis and anti-platelet aggregation, etc., as well as refreshing, enhancing memory, improving tension and drowsiness And other effects. 3. Cosmetics field: used in skin care products can play a role in removing stains, antioxidant, increasing skin elasticity, delaying aging, etc.; used in shampoo hair care products, can promote scalp blood circulation, improve hair loss, reduce the occurrence of dandruff and stimulate hair growth, moisten hair. Therefore, rosmarinic acid can be used as an excellent additive in cosmetics. |
| Rosemary plants | Rosemary plants are Lamiaceae, Rosemary. Small evergreen shrubs. About 1 meter high, young branches with 4 ribs, closely arranged, densely hairy; leaves opposite, sessile, leathery, linear, dark green on the surface, smooth, off-white fine tomentose on the back; flowers bisexual, short pedicels grow in pairs, axillary, calyx bell-shaped, 2 lips, upper lip entire, lower lip bifid, corolla 3 times longer than calyx, 2 lips, upper lip deeply concave bifid, the lower lip is three-lobed to the middle of the lobe, and the pregnant stamens 2 protrude out of the flower. The flower is light blue, occasionally pink or white, blooms in spring and has a strong aroma. Rosemary plants are native to North Africa. After Zhang Qian passed through the Western Regions, they were introduced to China from the Western Regions. It is a traditional commodity for the Roman Empire, the Eastern Roman Empire and China to trade, so the Chinese also call it "Daqin Fragrance". This product is a herb for both medicine and food. It has an oleosome, which can be used for viewing and extracting fragrance. Rosemary twigs and flower buds can also extract aromatic oil. This aromatic oil can be used to mix food flavors, to mix seasonings, and to make small companies. Rosemary is rarely used in Chinese as an edible seasoning. It is mainly used in Western food. It is quite common in Europe. So far, rosemary is still a very popular cooking seasoning in Europe. pictures of rosemary plants |
| antibacterial effect | rosmarinic acid has broad-spectrum antimicrobial activity and has inhibitory effect on bacteria and fungi. Rosmarinic acid has obvious inhibitory effect on bacteria such as Bacillus subtilis, Bacillus luteus, Escherichia coli, Staphylococcus aureus and Bacillus solani. Neusa et al. found that rosmarinic acid can inhibit the growth and biofilm formation of Streptococcus caries and Streptococcus mutans, and reduce their glucosyltransferase activity, indicating that rosmarinic acid can be used for the prevention and treatment of oral diseases. The study of the antibacterial mechanism of rosmarinic acid shows that on the one hand, rosmarinic acid can increase the permeability of bacterial cell membranes, cause a large amount of carbohydrate and protein leakage, and affect the normal metabolism of bacteria; on the other hand, it can also affect the protein metabolism of bacteria, It also has an inhibitory effect on Taq DNA polymerase. Guo Dawson et al. studied the inhibitory activity of rosmarinic acid on the mycelial growth and spore germination of different plant pathogenic fungi, and found that rosmarinic acid has a strong inhibitory effect on the mycelial growth of tomato gray mold, mango gray spot fungus, Citrus Penicillium and pear black spot fungus, and the strongest inhibitory effect on the spore germination of pear black spot fungus. Rosmarinic acid has antibacterial activity against gram-negative bacteria Escherichia coli and gram-positive bacteria Staphylococcus aureus, but the sensitivity of Staphylococcus aureus to rosmarinic acid is significantly higher than that of Escherichia coli. The experimental results also show that rosmarinic acid can significantly increase the permeability of bacterial cell membranes, accelerate the leakage of carbohydrates and proteins, and cause cell metabolism disorders; rosmarinic acid can also affect bacterial protein metabolism. Compared with the total protein of Staphylococcus aureus before and after rosmarinic acid treatment, it can be seen that the treatment of rosmarinic acid promotes the degradation of certain proteins in the process of bacterial metabolism, or promotes the synthesis of certain stress proteins in a short period of time. As for what specific protein rosmarinic acid acts on, it needs to be further determined. From the experimental results of the interaction between rosmarinic acid and plasmid DNA, it can be seen that rosmarinic acid has no interaction with DNA, so it can be inferred that it cannot bind to the primers in the polymerase chain reaction system. The inhibition of the polymerase chain reaction is because the compound inhibits the activity of DNA polymerase binding, thereby inhibiting DNA replication. To sum up, rosmarinic acid has certain effects on cell membrane permeability, protein metabolism and DNA replication of bacteria, thus exerting its antibacterial effect. |
| antioxidant effect | rosmarinic acid has strong activity of scavenging free radicals and antioxidant effect in vivo. Studies have shown that its mechanism of action is: rosmarinic acid and unsaturated fatty acids are competitively combined with lipid peroxy groups to finally stop the chain reaction of lipid peroxidation and reduce the rate of lipid peroxidation, while rosmarinic acid is oxidized to quinone; Acinic acid can inhibit the respiratory burst of neutrophils and inhibit the release of lysosomes by reducing the concentration of intracellular calcium ions; inhibit the oxidation of low-density lipoprotein regulated by endothelial cells. the antioxidant effect of rosmarinic acid is related to its structure. Nakamura and others believe that o-diphenol hydroxyl is the material basis of free radical scavenging activity. And the conjugate double bond of the C3 bit has a synergistic effect. |
| antidepressant effect | rosmarinic acid has antidepressant effect on animal models of depression. ItoN et al. conducted experiments on the cell proliferation of the horse's gyrus in the mind of mice, and used bromodeoxyuridine antibodies for immunohistochemical analysis to explore its mechanism of action. It was found that in the rosmarinic acid treatment group, the labeled value-added cells increased, combined with depression The forced swimming test of animal models showed that rosmarinic acid proliferated at least partially through the newborn cells of the hippocampus and produced an antidepressant-like effect. |
| stability | the results of the study on the stability of rosmarinic acid show that rosmarinic acid has better stability. Salt and sucrose have no effect on the stability of rosmarinic acid; pH and temperature have little effect on the stability of rosmarinic acid, and the results show that rosmarinic acid is more suitable for storage and use under acidic and low temperature conditions; light has a greater effect on rosmarinic acid, so it should be used as far as possible to avoid light; Ca2 and Mg2 have a greater effect on the stability of rosmarinic acid, and other metal ions have less effect on rosmarinic acid, contact with calcium and magnesium should be avoided when using; low-concentration sodium benzoate and potassium sorbate have little effect on the stability of rosmarinic acid, and should be added in accordance with the hygienic standards of food additives; ascorbic acid has a certain effect on rosmarinic acid, and the effect of low concentration is small; the oxidant hydrogen peroxide has a great effect on rosmarinic acid; the reducing agent sodium metabisulfite has a small effect on rosmarinic acid. |
| rosemary | rosemary is a spice plant with a long history native to the Mediterranean coast. it was first introduced into China by the Chinese academy of sciences in 1981 and successfully cultivated it. it is now planted in Yunnan, Hunan, Sichuan, Guizhou, Guangxi and other places. Rosemary is a rare natural spice plant, which emits a faint scent during the growing season and has the effect of refreshing and refreshing. Its stems, leaves and flowers have a pleasant fragrance. The aromatic oil extracted from flowers and twigs can be used to prepare air cleaners, perfumes, soaps and other cosmetic raw materials. The most famous toner is made of rosemary and can be used in beverages., Skin care oil, hair grower, laundry cream. As a drug, it can be used to treat neurological diseases and make ointment for headache and rheumatism. In recent years, it has been discovered that it is still an ideal natural preservative. It can also be used as an ornamental plant or a potted plant. Rosemary is a multi-purpose cash crop, from which antioxidants, rosemary essential oil and pharmaceutical intermediates can be extracted. Antioxidants are powdered substances extracted from rosemary plants. The main components are phenols, acids and flavonoids with antioxidant functions. rosemary essential oil is a liquid oil composed of more than 30 volatile components. Rosmarinic acid, a powdered substance extracted from rosemary, has high efficiency and non-toxic antioxidant effect, and can be widely used in food, functional food, spices and condiments, daily chemical industries and other industries. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: antioxidant, anti-aging, strong weight loss and lipid-lowering effects, treatment of cardiovascular diseases and anti-cancer. a biologically active plant phenolic compound with antioxidant and anti-inflammatory effects. |
Last Update：2024-04-09 19:05:10
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