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CAS NO.404-86-4
98%(1-25)Kilogram98%(26-500)Kilogram98%(501-1000)Kilogram
capsaicin
CAS: 404-86-4
Molecular Formula: C18H27NO3
| Name | capsaicin |
| Synonyms | CAPSAICIN FEMA 3404 capsaicin Capsaicine CAPSAICINE (E)-CAPSAICIN CAPSAICIN, NATURAL (E)-N-([4-HYDROXY-3-METHOXYPHENYL]METHYL)8-METHYL-6-NONEAMIDE (E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDE (E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE |
| CAS | 404-86-4 |
| EINECS | 206-969-8 |
| InChI | InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+ |
| InChIKey | YKPUWZUDDOIDPM-SOFGYWHQSA-N |
| Molecular Formula | C18H27NO3 |
| Molar Mass | 305.41 |
| Density | 1.1037 (rough estimate) |
| Melting Point | 62-65°C(lit.) |
| Boling Point | 210-220 C |
| Flash Point | 113°C |
| Water Solubility | insoluble |
| Solubility | Easily soluble in organic solvents such as ethanol, ether, acetone, benzene and chloroform, hot water and dilute alkali solution, slightly soluble in carbon disulfide, hardly soluble in cold water |
| Appearance | White powder or crystal |
| Color | Off-white |
| Merck | 14,1768 |
| BRN | 2816484 |
| pKa | 9.76±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5100 (estimate) |
| MDL | MFCD00017259 |
| Physical and Chemical Properties | Soluble in chloroform derived from capsicum |
| Risk Codes | R25 - Toxic if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R42/43 - May cause sensitization by inhalation and skin contact. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/39 - S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | RA8530000 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29399990 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 oral in mouse: 47200ug/kg |
| Overview | Capsaicin is also called capsaicin or capsaicin, and its chemical name is trans -8-methyl-N-vanillyl -6-nonenyl amide. It is an extremely spicy vanillamide alkaloid in pepper. It has antibacterial, antioxidant, anti-tumor, anti-inflammatory and analgesic effects, it is widely used in food and health care, medicine, planting, aquaculture, coating industry, military and other fields, and has high application value. natural capsaicin (Capsaicinoids) is composed of a series of similar substances. 19 kinds of similar substances have been found. they all have a common structure. they were first extracted from chili peppers by Thresh in 1876. they are spicy substances in chili peppers. It has the effects of analgesic, anti-cancer, regulating blood lipids, antibacterial and anti-inflammatory, weight loss, anti-fatigue, analgesic, antipruritic, anti-inflammatory, antioxidant, myocardial protection and regulating blood pressure. It can also cause skin vasodilation and improve microcirculation. It can also use its irritating spicy taste to produce a series of physiological reactions and repellent effects on humans and animals. Therefore, it has a wide range of applications, mainly in medical treatment, beauty, biological control, food additives, military and other fields. |
| pharmacological action | capsaicin has the following effects: 1. analgesic effect; 2. cardiovascular protective effect; 3. anticancer effect; 4. effect on digestive system; 5. anti-itching effect; 6. antibacterial and insecticidal effect. 1. prevention of cardiovascular diseases if low-density lipoprotein (LDL) is oxidized, the generated oxidized low-density lipoprotein will block the arteries and lead to atherosclerosis. Capsaicin is a potential antioxidant. Capsaicin is an effective vasodilator and diuretic for hypertensive model mice caused by salt. It can maintain normal blood pressure by balancing the nervous and hormonal systems. Calcitonin gene-related peptide (Calcitonin gene-related peptide , CGRP) is a peptide substance released by capsaicin-sensitive sensory nerve endings, which is related to cardiovascular diseases, especially hypertension. 2. prevention and treatment of digestive tract diseases capsaicin-sensitive afferent nerve plays an important role in gastric mucosal defense mechanism. Capsaicin can stimulate the afferent nerve and improve the release of CGRP and P substance in the stomach to protect the gastric mucosa. Capsicum capsicum sensitivity perception nerve plays an important role in mucosal defense institutions through the regulation process of gastric function such as mucosal blood flow and gastric peristalsis. It not only protects the gastric mucosa when it is injured, but also is conducive to the healing of the injury. Capsaicin can stimulate the oral mucosa to increase salivary secretion of amylase, reflexively increase the movement of the stomach, improve the activity of digestive enzymes, improve digestive function. 3. impact on respiratory diseases if a person does not wear a gas mask and is exposed to 0.5~1.0 ppm chlorine for 15min, nasal obstruction reaction will be caused. Rats also have a direct nasal obstruction response similar to human. However, pretreatment with capsaicin can significantly reduce the irritability and nasal obstruction response of mice to chlorine. 4. analgesic the effect of capsaicin on sensory nerves is manifested as topical application capsaicin can desensitize the body to stimuli such as pain and itching without affecting mechanical stimulation threshold, such as temperature, pressure or tactile stimulation. Capsaicin can be used as a typical analgesic for the treatment of different pain conditions, which can reduce and improve pain that patients cannot or rarely control with other methods. 5. anti-cancer capsaicin can change the gene-related expression of tumor. Capsaicin can inhibit the lipid peroxidation of aflatoxin B1 to the liver, thus reducing its damage to the liver. Capsaicin is effective in the treatment of human hepatoma. Capsicum has anti-male prostate cancer cells, and capsaicin is expected to be a substitute for chemical drugs for the treatment of prostate cancer. 6. weight loss capsaicin can promote lipid metabolism, dissolve fat and inhibit fat accumulation in the body. After entering the human body, capsaicin can promote the secretion of neurotransmitters acetylcholine and norepinephrine, and epinephrine can play a more effective role in weight loss through sweating and burning fat. 7. treat chilblain and baldness capsaicin can dilate blood vessels and promote microcirculation and hair growth. 8. other effects prurigo (Prurigo) is a general term for a group of acute or chronic inflammatory skin diseases. It is a skin disease that predisposes to itching on the extension of the limbs. Its triggering mechanism is still unclear. Most of them believe that it may be related to allergic reactions. Capsaicin stimulation of nerve release CGRP and SP is effective in the treatment of cutaneous neuroinflammation and prurigo. capsaicin can enhance the spontaneous discharge activity of renal-human fibers. capsaicin has the therapeutic effect of compensatory ovarian hypertrophy (compensatory ovarian hypertrophy ,COH) and compensatory ovulation (compensatory ovulation,CO) on adult female mice with uterus removed. Capsaicin has an inhibitory effect on many bacteria and can also inhibit fungi. It is safer than chemical preservatives and has nutritional effects. Pepper is a broad-spectrum antibacterial natural preservative, and has the characteristics of health, green and environmental protection. Ma pepper has a good anti-fatigue effect. |
| drug overview | name: natural capsaicin also known as: capsaicin substances chemical structure general formula: H3CO(HO)-C6H3-CH2-NH-CO-R fig. 1 is the structural formula of natural capsaicin |
| Source | Capsaicin (capsaicin) is a vanillamide alkaloid widely found in the Solanaceae pepper, especially red pepper. |
| plant morphology | annual or limited perennial; 40~80cm high; The stem branches are slightly zigzag and curved. The leaves are alternate, the top nodes of the branches are not elongated into twins or clusters, rectangular oval or ovate-lanceolate, 4~13cm long, 1.5~4cm wide, the top is acuminate, and the base is narrow and wedge-shaped; the petiole is 4~7cm long. Flowers solitary, prostrate; calyx cupular, inconspicuous 5-toothed; corolla white, lobes ovate; anthers gray-purple. The fruit stalk is thicker and drooping; the fruit is long finger-shaped, the top is acuminate and often curved, green when immature, and mature into red, orange or purple-red, with a spicy taste. The seeds are flat kidney-shaped, 3 ~ 5mm long, and light yellow. The flower and fruit period is from May to November. |
| chemical composition | natural capsaicin (Capsaicinoids) is composed of a series of congeners. 19 analogs have been found, all of which have a common part of the structure and all have spicy taste. It is mainly composed of 69% capsaicin (capsaicin), 22% dihydrocapsaicin (dihydrocapsaicin) and 7% dihydrocapsaicin (nordi-hydrocapsaicin), 1% high dihydrocapsaicin (homodihydrocapsaicin) and 1% high capsaicin (homcapsaicin). The contents of capsaicin and dihydrocapsaicin account for more than 90% of the total capsaicin content. |
| extraction method | 1. solvent extraction method solvent extraction method is obtained by pulverizing chili peel with single solvent or mixed solvent such as petroleum ether, ethanol, acetone, stirring at room temperature, leaching and filtering several times. For example, capsicum extract is used as raw material, extracted with 10% sodium hydroxide solution, extracted under stirring at 60 ℃ for 5h, left to layer, add dilute hydrochloric acid to the lower layer of water, adjust the pH to 5, extract petroleum ether and acetone twice, concentrate and crystallize, and obtain a crude capsicum compound product with a yield of 70.64% and a purity of 93.5% after recrystallization with ether. 2. ultrasonic extraction method compared with the traditional extraction method, the ultrasonic extraction process has the advantages of high yield, short production cycle, no heating, and no damage to the effective components. For example, under the technological conditions of solid-liquid ratio of 1:15, 70% ethanol as extraction solvent, extraction temperature of 60 ℃, ultrasonic frequency of 28kHz, power of 120W, extraction time of 20min, capsaicin yield of 2.819 mg/g, primary extraction rate of 64.2%, and continuous extraction rate of 3 times reached 89.4%, which was nearly 20% higher than that of traditional ethanol solvent extraction method. 3. microwave-assisted extraction capsaicin was extracted by acetic acid-microwave pretreatment. 1mL 10% acetic acid was used as gasification agent for each gram of chili powder, soaked for 15min, pretreated with 480W microwave power for 90s, then 8mL 50% acetic acid was used for 50 ℃ for 50min, and the extraction rate reached 6.62 mg/g. 4. Supercritical fluid extraction |
Mol Download Chemical properties
CAS:
404-86-4
MF:
C18H27NO3
MW:
305.41
EINECS:
206-969-8
MDL No.:
MFCD00017259
Melting point:
62-65 °C(lit.)
Boiling point:
210-220 C
Density
1.1037 (rough estimate)
FEMA
refractive index
1.5100 (estimate)
Flash point:
113 °C
storage temp.
2-8°C
solubility
H2O: insoluble
pka
9.76±0.20(Predicted)
form
Off-white solid
color
Off-white
Odor
mild warm herbal
Odor Type
herbal
Water Solubility
insoluble
Merck
14,1768
BRN
2816484
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
YKPUWZUDDOIDPM-SOFGYWHQSA-N
LogP
4.00
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