Synephrine
synephrine
CAS: 94-07-5;575-81-5
Molecular Formula: C9H13NO2
Synephrine - Names and Identifiers
| Name | synephrine |
| Synonyms | oxedrine SYNEPHRINE synephrine Synephrine SYNEPHERINE AKOS NCG1-0008 2-[1-hydroxy-2-(methylamino)ethyl]phenol 4-(1-hydroxy-2-(methylamino)ethyl)phenol 1-[4-HYDROXYPHENYL]-2-METHYLAMINOETHANOL 4-Hydroxy-alpha-(methylaminomethyl)benzyl 4-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol 4-hydroxy-alpha-(methylaminomethyl)benzyl alcohol |
| CAS | 94-07-5 575-81-5 |
| EINECS | 202-300-9 |
| InChI | InChI=1/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1 |
Synephrine - Physico-chemical Properties
| Molecular Formula | C9H13NO2 |
| Molar Mass | 167.21 |
| Density | 1.1222 (rough estimate) |
| Melting Point | 187°C (dec.)(lit.) |
| Boling Point | 295.79°C (rough estimate) |
| Flash Point | 163.4°C |
| Solubility | Easily soluble in water, hardly soluble in ether, |
| Vapor Presure | 3.18E-05mmHg at 25°C |
| Appearance | Colorless crystal (ethanol-ether) |
| Color | White to Off-White |
| Merck | 14,9012 |
| pKa | pKa 9.60±0.02(H2Ot = 25.0±0.5I = 0.01)(Approximate) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.4680 (estimate) |
| MDL | MFCD00002370 |
| Physical and Chemical Properties | Hydrochloride, colorless crystal (ethanol-ether), melting point: 166 ℃-167 ℃,[α]27D-52. (C = 7.6 mg/ml, anhydrous methanol). In strong acid, strong base ion exchange resin chromatography separation is prone to racemization. Crystallization, melting point: 184 ℃-185 ℃; Hydrochloride crystallization, melting point: 151 ℃-152 ℃, easily soluble in water; Btartrate, 188 ℃-189 ℃ (partial decomposition), easily soluble in water, hardly soluble in ether, almost insoluble in chloroform and ether. |
| Use | Used as a vasopressor |
Synephrine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | DO7350000 |
| HS Code | 29225090 |
Synephrine - Reference
| Reference Show more | 1. [IF=5.64] Wu Dousheng et al."Oleanolic Acid Induces the Type III Secretion System of Ralstonia solanacearum."Front Microbiol. 2015 Dec;0:1466 2. [IF=4.411] Liuyi Yu et al."Systematic Detection and Identification of Bioactive Ingredients from Citrus aurantium L. var. amara Using HPLC-Q-TOF-MS Combined with a Screening Method."Molecules. 2020 Jan;25(2):357 3. [IF=4.411] Simona S. Ghanem et al."Natural Alkaloid Compounds as Inhibitors for Alpha-Synuclein Seeded Fibril Formation and Toxicity."Molecules. 2021 Jan;26(12):3736 |
Synephrine - Reference Information
| Plant Source: | fructus aurantii immaturus |
| Character | White needle-like crystalline powder; Slightly gas, bitter. |
| plant extract | synephrine a biologically active substance, mainly from fructus aurantii, pericarpium citri reticulatae, green husk and other Rutaceae plant extract, is the effective component of traditional Chinese medicine fructus aurantii immaturus play an important role, with strong heart, increase the amount of cardiac output, contraction of blood vessels, high total peripheral vascular resistance to the left ventricular pressure and arterial blood pressure to rise the role of anti-Shock and the role of weight loss, but because of the structure of synephrine similar to the jute base with the excitation of central nervous, the potential side effects that lead to cardiovascular disease have been restricted in recent years in the United States, Canada and other countries. Figure 1 shows the extract of Citrus aurantium, synephrine |
| pharmacological effects | The pharmacological effects of synephrine are mainly adrenergic receptor agonists, heart receptors also have a certain Excitatory effect; Can shrink blood vessels, hypertension, expansion of bronchial and tracheal; Also has a certain weight loss, antidepressant effect, clinically, it is mainly used for the treatment of bronchial asthma and hypotension collapse and Shock orthostatic hypotension accumulation of stomach drop, synephrine is a pure natural stimulant, without any side effects and positive reaction, has been widely used in pharmaceutical food and beverage industries. |
| separation and extraction methods | at present, there is no report on the mature process for the extraction and separation of high purity synephrine, and more commonly used methods are mainly cation beam transesterification and hydrochloric acid percolation method. The market demand for Citrus aurantium extract and hesperidin containing synephrine is large. Therefore, it is necessary to establish a comprehensive utilization process of Citrus aurantium, and extract synephrine and hesperidin from Citrus aurantium step by step. |
| analytical method of content | as the market demand for synephrine increases, the value of synephrine doubles, for its content detection methods and other aspects of the research is also in-depth, the current reported methods are (1) reversed-phase high performance liquid chromatography (RP-HPLC), (2) packed column Supercritical fluid chromatography (SFC), (3)HPLC method, (4) thin layer scanning method, (5) high performance liquid chromatography and thin layer chromatography scanning method, etc. |
| determination of synephrine content in fructus aurantii of Rutaceae family by HPLC | [sample] Dried and mature pericarp of orange Citrus teticullocally and its cultivars, the medicinal herbs are named "Tangerine Peel" and "pericarpium citri reticulatae", or Citrus aurantiwm L. And its cultivated varieties of dried immature fruit, or sweet orange C. The dried young fruit of sinensis Osbeck, the medicinal material is called fructus aurantii; Or the pericarp of the dried young fruit or immature fruit of orange and its cultivated varieties, the medicinal material is called green husk. (1) chromatographic conditions column: Micropak MCH-5C18; Mobile phase: methanol solution of 0.02mol/L phosphoric acid and 0.2% sodium dodecyl sulfate; Column temperature: 50 ℃; Flow rate: 1 ml/min; detection wavelength: 275nm. (2) preparation of reference solution 4mg of synephrine reference was obtained by dissolving and diluting to 10ml with 0.01mol/L hydrochloric acid. (3) preparation of sample solution take 1g of sample fine powder, weigh it finely, put it in a 50ml plug Erlenmeyer flask, add 20ml of methanol, pack it, extract it with ultrasonic oscillation for 15min, and let it stand for 4H, filter, add 5ml of the filtrate to a 10ml plug centrifuge tube, imdissolve and evaporate to dryness at 90 ℃, cool, add 2ml of 0.01mol/L hydrochloric acid and 2ml of chloroform, plug and shake, centrifuge, the supernatant was taken for use. (4) measurement: 10ml of each of the sample solution and the reference sample solution were accurately extracted, injected, and measured according to chromatographic conditions. (5) determination results FIG. 2 shows the content of synephrine (n = 6,%) |
| Use | vasopressor. For Shock, for heart failure, treatment of bronchial asthma and surgery and anesthesia at the end of blood pressure, collapse and Shock, body, low blood pressure, etc. used as vasopressor α-adrenoceptor agonist, vasoconstrictor. |
| production method | the results of the Rutaceae plant Citrus aurantium L. |
Last Update：2024-04-09 20:48:19
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