(4aR,10aα)-1,3,4,9,10,10a-Hexahydro-5,6,9α-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10β,4aβ-(epoxymethano)phenanthren-12-one
rosmanol
CAS: 80225-53-2
Molecular Formula: C20H26O5
(4aR,10aα)-1,3,4,9,10,10a-Hexahydro-5,6,9α-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10β,4aβ-(epoxymethano)phenanthren-12-one - Names and Identifiers
(4aR,10aα)-1,3,4,9,10,10a-Hexahydro-5,6,9α-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10β,4aβ-(epoxymethano)phenanthren-12-one - Physico-chemical Properties
| Molecular Formula | C20H26O5 |
| Molar Mass | 346.42 |
| Density | 1.33 |
| Melting Point | 212-213 °C(Solv: ethyl ether (60-29-7)) |
| Boling Point | 574.2±50.0 °C(Predicted) |
| Flash Point | 205.663°C |
| Solubility | Soluble in methanol, ethyl acetate, slightly soluble in petroleum ether, insoluble in water |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White granular crystal |
| pKa | 9.07±0.60(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.625 |
| MDL | MFCD12031636 |
(4aR,10aα)-1,3,4,9,10,10a-Hexahydro-5,6,9α-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10β,4aβ-(epoxymethano)phenanthren-12-one - Reference
| Reference Show more | 1. [IF=2.72] Ji-Yu Nie et al."Antioxidant activity evaluation of rosemary ethanol extract and their cellular antioxidant activity toward HeLa cells."J Food Biochem. 2019 Jul;43(7):e12851 |
(4aR,10aα)-1,3,4,9,10,10a-Hexahydro-5,6,9α-trihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-10β,4aβ-(epoxymethano)phenanthren-12-one - Reference Information
| plant extract | rosmarinic acid is a water-soluble, it is widely distributed, mainly in the Labiatae, lithospermum, Cucurbitaceae, lindaceae, Umbelliferae plants, especially in labiaceae and Lithospermum plants with the highest content. rosmarinic acid is a natural antioxidant, with strong antioxidant activity, its antioxidant activity is stronger than vitamin E, caffeic acid, chlorogenic acid, folic acid and so on, which helps to prevent cell damage caused by free radicals, thus the risk of cancer and arteriosclerosis is reduced. rosmarinic acid has strong anti-inflammatory activity, at the same time rosmarinic acid also has antibacterial, antiviral, antitumor activity, and has the ability to inhibit acute and chronic infection, anti-ultraviolet, properties such as inhibition of elastin degradation have made rosmarinic acid an additive in cosmetics. At present, rosmarinic acid has shown its important application value in pharmaceutical, food, cosmetics and other fields. In conclusion, rosmarinic acid has very broad application prospects and market value, the main application areas: 1. Food Field: rosmarinic acid, as a natural and efficient antioxidant, can replace BHA and BHT in animal and vegetable fats and oils, dairy products, oil-rich foods, sweets and baked foods; it can also be used as a spice in various kinds of soup and flavored food; And has antiseptic and antibacterial effect. In Japan, perilla extract rich in rosmarinic acid is used as a decoration to improve the shelf life of fresh seafood. 2. Health care products: anti-tumor, anti-hepatitis and protection of liver injury, role, anti-nephritis, anti-thrombosis and anti-platelet aggregation, etc., as well as refreshing, enhance memory, improve Nervousness mood and lethargy and other effects. 3. In the field of cosmetics: used in skin care products can play a stain, antioxidant, increase skin elasticity, anti-aging and other effects; 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. |
| antibacterial effect | rosmarinic acid has broad-spectrum antimicrobial activity, and has inhibitory effect on bacteria and fungi. Rosmarinic acid has obvious inhibitory effect on Bacillus subtilis, Micrococcus luteus, Escherichia coli, Staphylococcus aureus and Rhizoctonia solani. Neusa et al. found that rosmarinic acid can inhibit the growth and biofilm formation of dental caries Streptococcus and Streptococcus mutans, and reduce their glucosyltransferase activity, indicating that rosmarinic acid can be used for the prevention and treatment of oral diseases. The antibacterial mechanism of rosmarinic acid shows that rosmarinic acid can increase the permeability of bacterial cell membrane, cause a large number of leakage of carbohydrates and proteins, and affect the normal metabolism of bacteria; On the other hand, it can also affect the protein metabolism of bacteria, it also inhibited Taq DNA polymerase. The inhibitory activity of rosmarinic acid on mycelial growth and spore germination of different plant pathogenic fungi was studied by Guo daosen et al, the mycelial growth inhibition of citrus Penicillium and pear black spot pathogen was strong, and the spore germination of pear black spot pathogen was the strongest. 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 was significantly higher than that of Escherichia coli. The experimental results also show that rosmarinic acid can significantly increase the permeability of bacterial cell membrane, accelerate the leakage of carbohydrates and proteins, and make the cell metabolism disorder; Rosmarinic acid can also affect the bacterial protein metabolism, compared with the total protein of Staphylococcus aureus before and after treatment with rosmarinic acid, the treatment of rosmarinic acid promoted the degradation of some proteins in the process of bacterial metabolism, or promoted the synthesis of some stress proteins in the short term. As to which specific protein rosmarinic acid acts, it has yet to be further determined. From the results of the interaction between rosmarinic acid and plasmid DNA, we can see that rosmarinic acid does not interact with DNA, so it can be inferred that it can not bind to the primers in the polymerase chain reaction system, rosmarinic acid inhibits the polymerase chain reaction because the compound inhibits DNA polymerase binding activity, thereby inhibiting DNA replication. In summary, rosmarinic acid has certain effects on cell membrane permeability, protein metabolism and DNA replication of bacteria, thus playing its inhibitory effect. |
| Antioxidant effect | rosmarinic acid has a strong free radical scavenging activity and antioxidant effect. Research shows that the mechanism is: rosmarinic acid and unsaturated fatty acid competitive combination with lipid peroxy group, in order to end stop lipid peroxidation chain reaction, reduce the rate of lipid peroxidation, rosmarinic acid is oxidized to the quinone form; Dianoic acid can inhibit the respiratory burst of neutrophils and inhibit the release of lysosomes by reducing the intracellular calcium concentration; Inhibit the oxidation of low density lipoprotein regulated by endothelial cells. The antioxidant effect of rosmarinic acid is related to its structure. Nakamura et al. believe that the O-diphenolic hydroxyl group is the material basis for scavenging free radicals. Moreover, the conjugated double bond at the C3 position has a synergistic effect. |
| antidepressant effect | rosmarinic acid has antidepressant effect on animal model of depression. ItoN et al carried out experiments on the cell proliferation of mouse brain gyrus, and carried out immunohistochemical analysis with bromodeoxyuridine antibody to explore its mechanism of action. It was found that the proliferation of labeled cells increased in the rosmarinic acid treatment group, in combination with the forced swimming test in an animal model of depression, rosmarinic acid was shown to proliferate and produce an antidepressant-like effect, at least in part, through hippocampal gyrus neonatal cell proliferation. |
| stability | the stability of rosmarinic acid was studied. Salt and sucrose had no effect on the stability of rosmarinic acid, but pH and temperature had little effect on the stability of rosmarinic acid; light has a great influence on rosmarinic acid, so it should be used as far as possible to avoid light; Ca2 and Mg2 have a great influence on the stability of rosmarinic acid, and other metal ions have little influence on rosmarinic acid, in the use of should avoid contact with calcium, magnesium; Low concentration of sodium benzoate, potassium sorbate on the stability of rosmarinic acid is small, the use of food additives should be in accordance with the health standards added; ascorbic acid had a certain effect on rosmarinic acid, and low concentration had little effect. Oxidant hydrogen peroxide had a great effect on rosmarinic acid. |
| Rosemary | The Labiatae plant rosemary (Rosmarinus officinalis) is a long-standing spice plant originating from the Mediterranean coast, in 1981, the Chinese Academy of Sciences was introduced into China for the first time and was successfully cultivated. Now Yunnan, Hunan, Sichuan, Guizhou, Guangxi and other places have been planted. Rosemary is a valuable natural spice plants, the growing season will emit a fragrance, a clear heart refreshing effect. Its stems, leaves and flowers have a pleasant fragrance, and the aromatic oil extracted from flowers and shoots can be used to prepare air cleaners, perfumes, soap and other cosmetic raw materials, the best known lotion is made with rosemary and can be used in beverages, skin oils, hair restorations, and laundry creams. As a drug for the treatment of neurological disorders and the production of the treatment of Head Pain, rheumatism ointment. In recent years, it has been found that it is also an ideal natural preservative. Can also be used as ornamental plants or potted plants. Rosemary is a multi-purpose commercial crop, from which antioxidants, rosemary essential oil and pharmaceutical intermediates can be extracted. antioxidant is a kind of powdery substance extracted from Rosemary, and its main components are phenolic, acid and flavonoid with antioxidant function. The essential oil of Rosemary is a liquid oil composed of more than 30 volatile components. rosmarinic acid, a powdery substance extracted from Rosemary, has high efficiency and non-toxic antioxidant effect, and can be widely used in food, functional food, spices, condiment and daily chemical industries. |
Last Update：2024-04-09 20:48:19
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