Carnosic acid
Carnosic acid
CAS: 3650-09-7;6537-80-8
Molecular Formula: C20H28O4
Carnosic acid - Names and Identifiers
| Name | Carnosic acid |
| Synonyms | salvin CarnosicAcid CARNOSIC ACID Carnosic acid CARNOSOLIC ACID CARNOSIC ACID(P) CARNOSIC ACID(P)(NOW AVAILABLE IN GRAM SIZES)(P) 11,12-dihydroxyabieta-8(14),9(11),12-trien-20-oic acid (5xi)-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-oic acid (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid (4aR-trans)-1,3,4,9,10,10a-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-4a(2H)-phenanthrenecarboxylic acid 4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)- |
| CAS | 3650-09-7 6537-80-8 |
| EINECS | 609-253-7 |
| InChI | InChI=1/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14?,20-/m1/s1 |
| InChIKey | QRYRORQUOLYVBU-VBKZILBWSA-N |
Carnosic acid - Physico-chemical Properties
| Molecular Formula | C20H28O4 |
| Molar Mass | 332.43 |
| Density | 1.184±0.06 g/cm3(Predicted) |
| Melting Point | 190°C(lit.) |
| Boling Point | 506.4±50.0 °C(Predicted) |
| Specific Rotation(α) | (c, 1.07 in MeOH)+191 |
| Flash Point | 274.2°C |
| Solubility | Soluble in oil and organic solvents such as ethanol, ethyl acetate, acetone, chloroform, etc., insoluble in water. |
| Vapor Presure | 4.45E-11mmHg at 25°C |
| Appearance | White or yellow white powder |
| Color | yellow |
| BRN | 2707918 |
| pKa | 4.14±0.40(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.575 |
| MDL | MFCD02259459 |
| Physical and Chemical Properties | From Rosmarinus Rosmarinus L., a plant of the genus Rosmarinus, Labiatae.. |
Carnosic acid - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29182900 |
Carnosic acid - Reference
| Reference Show more | 1. Cai Xiaojun, Sun Yang win, Pan daodong, etc. Inhibitory mechanism of the main components of Rosemary against salmonella [J]. Chinese Journal of Food Science, 2019, 19(03):134-140. 2. Yao Mengying, kuangting, Yun Yonghuan, Cao Jun, Zhang Weiming. Effects of carnosic acid on main physicochemical properties, fatty acid composition and free radicals of coconut oil during thermal processing [J]. China Oil & Fat, 2020,45(08):39-44. 3. Jia Guokai, Liu Jia, Luo Mei, etc. Decolorization of carnosic acid by macroporous resin [J]. Science and Technology Innovation Review, 2016(13):33-34. 4. Yao Mengying, kuangting, Yun Yonghuan, Cao Jun, Zhang Weiming. Effects of carnosic acid on main physicochemical properties, fatty acid composition and free radicals of coconut oil during thermal processing [J]. China Oil & Fat, 2020,45(08):39-44. 5. Ren Shaodong, Wang qunxia, Ren Xiaoyu. Effects of different antioxidants on the quality of roasted meat products [J]. Meat Research, 2020,34(08):21-28. 6. Wenwen, Wang Wenqing, Wu Hua, Wang Chunling, Chen Xiaodi, Xu Min, Xiao Junsong. Antioxidant effect of fat-soluble Rosemary antioxidant on oil and fresh pork [J]. China Oils, 2021,46(03):142-148. 7. Xin Liu et al. [IF = 5.875]. "Transferrin-conjucted liposomes loaded with carnosic acid inhibitor cancer growth by inducing mitochondria-mediated apoptosis." Int J Pharmaceut. 2021 Sep;607:121034 8. [IF = 4.35] Jing Wei et al."A Deep Insight in the Antioxidant Property of Carnosic Acid: From Computational Study to Experimental Analysis."Foods. 2021 Oct;10(10):2279 |
Carnosic acid - Reference Information
| Plant source: | Rosemary |
| rosemary extract | sage acid is a diterpenoid compound isolated from the leaves of the plant rosemary Rosmarinus officinalis, white or yellow-white powder, Soluble in oil and organic solvents such as ethanol, ethyl acetate, acetone, chloroform, and insoluble in water. Sage acid is suitable for the antioxidant of oil-soluble components. Used in seasoning sauce, pet food and feed, it has antioxidant and anti-aging effects; strong weight loss and lipid-lowering effects; treatment of cardiovascular diseases and anti-cancer effects. Rosemary (Rosemarinus), a herbaceous plant of the Lamiaceae family, is native to southern European countries. It has been introduced and cultivated in Hunan, Guizhou, Hainan, Guangxi, Guangdong and other provinces and cities in my country. It contains carnosic acid, rosmarinol, rosmarinol, rosmarinol, rosmarinol, rosmarinol, rosmarinol and other effective ingredients. Among them, the high-efficiency antioxidants are carnosic acid, rosmarinol and sage. Phenol and so on. Fat-soluble rosemary extract is light yellow to yellowish brown powder or brown paste, insoluble in water, soluble in ethanol and oil; water-soluble rosemary extract is brown powder, with rosemary unique smell. Heat resistance (stable at 200 ℃), good UV resistance, and can effectively prevent oxidation of grease. Rosemary extract can be divided into oil-soluble (antioxidants) and water-soluble (antioxidants and preservatives). The active ingredient is mainly sage acid, and the latter is mainly rosemary phenol. Rosemary extract is natural and non-toxic, and its antioxidant effect is much higher than the existing natural antioxidants such as vitamin C, vitamin E, and tea polyphenols. It is 2 to 4 times that of synthetic antioxidants BHA and BHT, and its structure It is stable and not easy to decompose. It can withstand high temperatures from 190°C to 240°C, which completely overcomes the fatal weakness of most natural antioxidants such as vitamin C and tea polyphenols when decomposed at high temperatures. Therefore, compared with other similar products, it has the advantage of being more efficient and broad-spectrum. Researchers found that the antioxidant activity of rosemary extract at 300mg/kg was equivalent to 200mg/kg BHA and greater than 100mg/kg tocopherol. Generally, its antioxidant capacity increases with the increase of the addition amount, but at high concentration, it can precipitate the oil and discolor the water-containing food. the antioxidant function of rosemary mainly lies in its ability to quench singlet oxygen, scavenging free radicals, chelating metal ions and organic acids. The above information is collected by Xiaonan. |
| pharmacological effects of sage acid | (1) antibacterial effects studies have shown that sage acid has different degrees of inhibitory effects on staphylococcus aureus, escherichia coli, bacillus subtilis and hanson's yeast, and can be used as food preservatives. (2) antioxidant effect sage acid has good free radical scavenging and antioxidant effects. Its DPPH, ABTS free radical scavenging ability and iron reduction and antioxidant ability are stronger than VE, slightly weaker than synthetic antioxidant TBHQ; Its reducing ability is stronger than VE and TBHQ. sage acid is fat-soluble, which can effectively inhibit the formation of peroxides of oils and fats and the decomposition of polyene fatty acids, thereby prolonging the shelf life of oils and fats. In addition, studies have found that sage acid can effectively remove oxygen free radicals in mouse liver cells and reduce the production of lipid peroxides, thereby stabilizing cell membranes; sage acid can also inhibit the oxidation reaction of low-density lipoprotein, which can effectively Prevent the occurrence of atherosclerosis. (3) other effects studies have found that carnosic acid has an inhibitory effect on the proliferation of HL-60 cells and is expected to become a new drug for the treatment of hematological malignant tumors, for the treatment of cardiovascular diseases and anti-cancer. Kaloustian and others introduced rosemary extracts such as sage acid have certain therapeutic effects on heart disease and respiratory diseases, have antibacterial effects, and can also inhibit HIV infection. Ninomiya and others reported that rosemary extracts such as sage acid can not only effectively regulate the absorption of fat to control people's weight, so as to achieve the purpose of weight loss, but also treat inflammation, treat throat pain, treat indigestion, prevent Alzheimer's disease, treat diabetes, and promote the production of nerve growth factor. |
| study on antioxidant mechanism of rosemary | firstly, sage acid and sage phenol were isolated and purified. the method is as follows: 500g of dried rosemary leaves are extracted with ethanol at room temperature, and the extract is concentrated to dryness under reduced pressure. The dry extract was mixed with 1L n-hexane, leached for 72h, filtered, and the filtrate was concentrated to 1/3 of the original volume under reduced pressure. Three times were extracted with 0.5L 5% NaHCO3, combined with NaHCO3 extract, and pH was adjusted to 2.2 with H3PO4. Then extract again with n-hexane, dry with Na2SO4, concentrate under reduced pressure until yellow-green crystals appear, and filter to obtain sage acid crystals. 2kg rosemary dry stems and leaves were crushed to 1cm segments, refluxed and extracted three times (2h, 1h, 1h) with 8 times of petroleum ether, filtered and concentrated to obtain 235g of petroleum ether extract, leached with 5% NaHCO3 solution, then acidified with 5% hydrochloric acid, extracted with ethyl acetate, and obtained 1.8g of extract. The extract was chromatography with silica gel column, eluted with petroleum ether-acetone gradient, and collected 100mL per portion, A total of 108 parts were collected, of which 46-62 parts were combined, and the chloroform-acetone (3:1) eluted by silica gel column chromatography, 100mL each part, 52 parts were collected, 21-23 parts were combined, and acetone recrystallized to obtain colorless needle-like sage phenol crystals. ESR method was used to analyze the scavenging effects of monomers on superoxide anion radicals, hydroxyl radicals and lipid radicals, and chemiluminescence method was used to analyze the scavenging effects of monomers on superoxide anion radicals and their protective effects on DNA damage. The experimental results show that the activity of the five compounds is concentration-dependent. The higher the concentration, the higher the activity and saturation. The order of IC50 values for the scavenging of O2-· and lipid free radicals of the five compounds is as follows: for the scavenging of O2-· measured by ESR method, sage acid> isosmarinol> rosmarinol> rosmarinol> epimarinol> sage phenol; measured by CL method, isosmarinol> sage acid> rosmarinol> epimarinol> sage phenol; For lipid free radicals, sage acid> isosemary phenol> rosemary phenol> table rosemary phenol> sage phenol. |
| quantitative study on effective components in rosemary supercritical extract | the contents of sage acid and sage phenol in the extract were determined by RP-HPLC method. with the increase of sage acid content, the scavenging rate of lipid free radicals was also increasing, and the correlation number between the two reached 0.8614, which was quite positive. There was no correlation between the clearance rate and the content of sage phenol. Therefore, it can be determined that the main active component of the supercritical extract for scavenging lipid free radicals is sage acid, with sage phenol playing a secondary role. Because the content of rosemary phenol, epirosemary phenol and isosemary phenol in rosemary extract is very small, no quantitative study has been carried out, but this does not mean that the three have no contribution to the antioxidant activity of rosemary. Studies on the scavenging effects of monomer compounds on various free radicals show that all three have quite strong activities, especially isosmarinol. Therefore, rosemary phenol, epirosemary phenol, and isosemary phenol should also be the active ingredients of rosemary's antioxidant activity. |
| quantitative study on effective components in organic solvent rosemary extract | five organic solvents with increasing lipophilicity, methanol, ethanol, acetone, petroleum ether and hexane, were selected to extract rosemary by water bath reflux method to obtain different extracts. The results showed that the content of sage phenol in different solvent extracts was not much different, while the content of sage acid was quite different. This shows that the extraction of sage acid can not be too strong or too weak solvent, because the use of strong polar solvent in the extraction process of sage acid degradation, solvent polarity is too weak sage acid solubility is low, disadvantageous to the extraction. This is the reason why the entrainer should be added during supercritical fluid extraction, because the solubility of CO2 is equivalent to hexane, and the solubility of sage acid is not high. After adding 95% ethanol, the yield of sage acid can be increased. If acetone can be used as entrainer, the effect may be better. For the extraction of sage acid, it can be extracted with a solvent with a larger polarity, and then extracted with a solvent with a smaller polarity, so as to achieve the purpose of concentration. the effects of the above three different extraction methods on the yield of sage acid and sage phenol were compared. the results showed that heating can improve the yield of sage acid, especially for solvents with weak polarity. Reference material: Tang Chunhong editor. Natural preservatives and antioxidants. Beijing: China Light Industry Press. 2010. Page 202-209. |
| application prospect of sage acid | sage acid is the main active ingredient of rosemary antioxidant approved for use in China. As a fat-soluble natural antioxidant, sage acid is far superior to synthetic antioxidants in stabilizing oils and fats., It can be used in fats and fat-containing foods, biomedicine, chemicals, cosmetics and feeds, etc., in addition to preventing or delaying the oxidation of fats or oily foods, improving the stability of food and extending the storage time of storage, it can also be used as a flavoring agent for meat and fish. In Japan, rosemary extract is used in high-temperature fried food to prevent oxidation effect and light deterioration after packaging. It can also be used in frozen food to inhibit fishy smell. In Europe, rosemary extract is also used to prevent oxidation of ham and sausage products. The new product of diluted seasoning oil added with rosemary extract is very suitable for meat products. Microherb after years of research, the use of modern traditional Chinese medicine extraction technology and advanced chromatographic separation technology successfully separated high purity 90% (Carnosic acid) and rosmarinic acid (rosmarinic acid) for pharmacological, toxicological and clinical application of experimental research and widely used in medicine and health care and daily chemical industry. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: suitable for the anti-oxidation of oil-soluble ingredients, with anti-oxidation and anti-aging effects; strong weight loss and lipid-lowering effects; treatment of cardiovascular diseases and anti-cancer effects. sage acid is a natural antioxidant component extracted from the plant rosemary. As a raw material for skin care products, it has long been sold in European and American countries. |
Last Update：2024-04-09 21:54:55
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Email: 3008007409@qq.com
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QQ: 3008007409
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Product Name: Carnosic Acid Visit Supplier Webpage Request for quotationCAS: 3650-09-7
Tel: +86-(0)731-84213302
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Mobile: +86 13875855783
QQ: 484702402
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