(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
capsaicin
CAS: 404-86-4
Molecular Formula: C18H27NO3
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Names and Identifiers
| 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 |
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Physico-chemical Properties
| 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 |
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Risk and Safety
| 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 |
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Reference
| Reference Show more | 1. Li Qian, Cheng Xuan, Che Guanda, etc. Effect of capsaicin on glucose uptake in 3T3-L1 preadipocytes [J]. Advances in modern biomedicine, 2016, 16(014):2601-2603. 2. He Shuai, Xie Dingyuan. Detection of capsaicinoids and analysis of pungency characteristics in Zhejiang vegetables [J]. Science and Technology of Food Industry, 2016, 37(004):80-86. 3. Yu Yonghao, Xie Dingyuan, Fang Yan, Fan Gang, Ding Lu. Optimization of orthogonal experiment for solid phase extraction and separation of capsaicin from capsicum oil [J]. China condiment, 2020,45(12):6-12. 4. Chu, Haihan, Meng Li, and Xiuchun Wang. "Capsaicin indents and autophagy in human melanoma cells." Oncology letters 17.6 (2019): 4827-4834.https:// doi.org/10.3892/ol.2019.10206 5. [IF = 5.64] Wu Dousheng et al."Oleanolic Acid Induces the Type III Secretion System of Ralstonia solanacearum."Front Microbiol. 2015 Dec;0:1466 6. [IF=1.871] Haihan Chu et al."Capsaicin induces apoptosis and autophagy in human melanoma cells."Oncol Lett. 2019 Jun;17(6):4827-4834 |
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Nature
Open Data Verified Data
- The appearance is brown-red, and the relative density is 1. 12. The pure product is a white needle-like crystal with a melting point of 62-65 °c. Insoluble in water, soluble in ethyl acetate, methanol, ethanol, etc. At room temperature and weak acid/weak base (pH 4~9) medium stability, easy decomposition at high temperature (>100 deg C).
- the dosage form includes a compound preparation of 9% capsaicin-nicotine microemulsion and 1.2% avix-capsaicin microemulsion.
Last Update：2024-01-02 23:10:35
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Preparation Method
Open Data Verified Data
It is present in the Solanaceae plant capsicum (Ca psi-cumum) and obtained by extraction of plant raw materials.
Last Update：2022-01-01 11:18:25
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Use
Open Data Verified Data
The main effect of botanical insecticides on insects is to destroy the information transmission of feeding hormones in the nervous system, so that the larvae lose the taste function and show the anti-feeding response, the insect once after feeding showed gastric toxicity. It is mainly used for pest control on fruit trees, vegetables and food crops, and has repellent effect on birds, voles and so on.
Last Update：2022-01-01 11:18:25
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Safety
Open Data Verified Data
- This product is of low toxicity. The acute oral LD50 of the preparation in rats was 562mg/kg, and the acute percutaneous LD50 was 2000mg/kg.
- the refined products have polyethylene packaging bags of lOOOg, 500g, lOOg and other specifications. Store in a cool, dry, dark place.
Last Update：2022-01-01 11:18:26
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE - Reference Information
| FEMA | 3404 | CAPSAICIN |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| 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 Supercritical fluid extraction is a relatively new extraction and separation technology, which effectively overcomes the shortcomings of traditional separation methods. It uses high-pressure gas above the critical temperature as a solvent to separate, extract and refine effective components. For example, by supercritical extraction of capsaicin from Xinjiang pepper, the extraction rate of capsaicin reached 5.0 mg/g, which was higher than that of traditional solvent extraction method, under the conditions of extraction pressure of 12MPa, extraction temperature of 45 ℃, separation temperature of 45 ℃, extraction time of 40min and entrainer of anhydrous ethanol solid-liquid ratio of 1:2. Supercritical extraction method has the characteristics of fast extraction speed, saving solvent and low impurity content, but the expensive equipment is an important factor restricting its industrial production. 5. Enzymatic extraction has been widely used in the extraction of plant active ingredients, such as enzymatic extraction of safflower yellow pigment and enzymatic extraction of flavonoids. Because capsaicin and other fat-soluble components exist in the uneven fibrous tissue of capsaicin skin, capsaicin can be dissolved by enzymatic hydrolysis of fibrous tissue. For example, capsaicin in dry red pepper was extracted by cellulase, and the enzymatic hydrolysis temperature was 55 ℃, the initial pH of the enzymatic hydrolysis solution was 5.4, the enzymatic hydrolysis time was 4h, and the enzyme amount was 2.5 mg/g pepper. The natural capsaicin yield was 7.65 mg/g pepper. Compared with the traditional ethanol extraction method, the yield increased by 33%. |
| purification method | at present, the most widely used methods for purification of capsaicin are macroporous adsorption resin column chromatography, chitosan resin method and ion exchange method. 1. Macroporous adsorption resin method Macroporous adsorption resin method for extracting useful components from plants has the characteristics of simple operation, low cost and high yield. It is a modern extraction and separation method for widely used natural products. For example, after the ethanol extract of pepper is extracted with dilute ethanol, capsaicin is enriched with aqueous ethanol as eluent by macroporous adsorption resin column. Using this method to extract spicy ingredients such as capsaicin has the advantages of high extraction rate and purity, low cost and simple method. 2. chitosan resin method chitosan is an alkaline polysaccharide, and the amino group can bind the phenol meridians of capsaicin. Using this property, chitosan resin was used to adsorb and purify the initial extract of capsaicin, and the purity and yield of capsaicin obtained after recrystallization were higher, and the cost was low, which was beneficial to industrial production. For example, capsaicin extracted from weak alkali solution is used to remove lipid, chitosan resin column is used for adsorption, ethanol elution and recrystallization of capsaicin crystals, and the purity is 91.2% by high performance liquid chromatography. At present, the production technology of capsaicin generally has the problems of complicated process, low extraction rate and low yield. The use of chitosan resin adsorption extraction, the process is simple, the price is low, the product purity is high, in the industrial production has a certain significance. 3. ion exchange method crude capsaicin is used as raw material, dissolved in 1% sodium hydroxide solution, acidified with 2% sulfuric acid to pH = 3.0, extracted, concentrated and crystallized with n-hexane to obtain crude capsaicin with purity of 82% ~ 84%, dissolved in sodium hydroxide solution, purified with anion exchange resin, ethanol-ethyl acetate (volume ratio 45:55) Mixed solvent desolution, concentration and crystallization can obtain high purity capsaicin with purity greater than 98.5%. |
| analysis method | commonly used qualitative analysis methods mainly include thin layer chromatography, infrared spectroscopy and ultraviolet spectroscopy. In addition, nuclear magnetic resonance hydrogen spectroscopy, nuclear magnetic resonance carbon spectroscopy and mass spectrometry are also often used to identify the structure of capsaicin substances and distinguish their homologs. commonly used quantitative analysis methods mainly include kjeldahl method, FAO ultraviolet double colorimetric method, molybdenum blue colorimetric method and sodium molybdenum nitrite colorimetric method. The spicy index of each homolog in capsaicin substances is quite different, and the above methods can only determine the overall composition of capsaicin substances, and cannot quantify the main spicy substances separately, so it cannot be used for pepper and its products. The spicy taste of the product is more accurate quantitative analysis and evaluation. |
| use | 1. biological control a. green grain storage rodent repellents with capsaicin as the main component have good repelling effect on rural grain storage rats, and the repelling effect of capsaicin containing 1% capsaicin can be maintained for more than 5 months. B. protection cables and optical cables the irritation of capsaicin will have repellent effect on animals, which can be used as a functional additive for anti-rat cable sheath plastics in cable and optical cable industries. When used in PVC, PE and other plastics, it can prevent mice and termites from damaging the food erosion of products c. antifouling coating biological antifouling coating made by using the repellent characteristics of capsaicin, it is applied to the parts of ships and marine buildings in contact with seawater, which can effectively prevent the attachment of marine life and the accumulation of aquatic life in the hull. At present, capsaicin has replaced organotin as a new type of anti-fouling coating for ships and marine buildings. d. biopesticide capsaicin can be used as a new type of green pesticide in the field of biopesticide. capsaicin has good contact killing and repellent effects, and can achieve the characteristics of high efficacy, long lasting effect and degradation for crop pest control. capsaicin is a new type of environmentally friendly biopesticide. 2. medical beauty a. medical capsaicin has significant curative effect on neuropathic pain, rheumatoid arthritis, fresh cowhide, psoriasis, acne, baldness, etc. Among them, analgesia is currently the most mature application of capsaicin research. Capsaicin can also be used in the prevention and treatment of cardiovascular and cerebrovascular diseases. In addition, capsaicin can also prevent peptic ulcer and respiratory diseases, and has special effects of weight loss, anti-fatigue and auxiliary detoxification. B. beauty can be used as a raw material for the production of beauty and skin care products to improve the skin quality of the face and arms, but different parts should pay attention to the difference in concentration. 3. other fields a. military capsaicin has a good tear gas effect, which can trigger a strong physiological reaction of the human body, causing people to cough, vomiting, tearing and other symptoms, and even lose their way, but it has no toxic side effects. therefore, capsaicin is the main raw material for making tear gas, tear gas guns and defense weapons in the military, and has been widely used in the United States, Japan, Germany, Southeast Asia and other countries. Capsaicin is also used as a personal self-defense weapon and a tool to subdue offenders. B. food additives can be used in the processing of various spicy foods in food workers, including various spicy fatty foods, daily condiments, spicy sauces, baked foods, etc. In addition, capsaicin has strong antibacterial and bactericidal properties, and has certain inhibitory effects on bacteria, fungi and yeasts, and can be used as a potential food preservative. Drugs for treating soft tissue injury. Active ingredients of pepper, capsaicin receptor agonist, neurotoxin; Activation of sensory neurons. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | abdominal cavity-rat LD50: 9.5 mg/kg; Oral administration-mouse LD50: 47.2 mg/kg |
| stimulation data | skin-human 1%/30 points mild; Eye-guinea pig 1 mg mild |
| flammability hazard characteristics | spicy choking; thermal decomposition discharges toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse low temperature ventilation and drying; separate from food raw materials |
| fire extinguishing agent | water, carbon dioxide, foam, dry powder |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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View History
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
3-(DIMETHYLAMINO)-1-[4-(4-METHOXYBENZOYL)-3-ISOXAZOLYL]-2-PROPEN-1-ONE
5-[(PHENYLMETHYL)THIO]-1H-TETRAZOLE (BMT)
LSD抑制剂24
Urea, N-[2-methoxy-5-[5-[4-(2-methoxyphenyl)-1-piperazinyl]-1-oxopentyl]phenyl]-
3-(DIMETHYLAMINO)-1-[4-(4-METHOXYBENZOYL)-3-ISOXAZOLYL]-2-PROPEN-1-ONE
5-[(PHENYLMETHYL)THIO]-1H-TETRAZOLE (BMT)
LSD抑制剂24
Urea, N-[2-methoxy-5-[5-[4-(2-methoxyphenyl)-1-piperazinyl]-1-oxopentyl]phenyl]-