Amygdalin 29883-15-6
D(-)-Amygdalin hydrate
CAS: 29883-15-6
Molecular Formula: C20H27NO11
Amygdalin 29883-15-6 - Names and Identifiers
| Name | D(-)-Amygdalin hydrate |
| Synonyms | (r)-y) (r)-oxy) amygdalin amygdaloside D-Amygdalin hydrate Amygdalin 29883-15-6 D-Amygdalin (1.12428) D(-)-Amygdalin hydrate (2R)-[(6-O-hexopyranosylhexopyranosyl)oxy](phenyl)ethanenitrile (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto benzeneacetonitrile,alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl) {[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}(phenyl)acetonitrile benzeneacetonitrile,alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)ox (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneacetonit (2R)-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}(phenyl)ethanenitrile |
| CAS | 29883-15-6 |
| EINECS | 249-925-3 |
| InChI | InChI=1/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1 |
| InChIKey | XUCIJNAGGSZNQT-SWRVSKMJSA-N |
Amygdalin 29883-15-6 - Physico-chemical Properties
| Molecular Formula | C20H27NO11 |
| Molar Mass | 457.43 |
| Density | 1.4474 (rough estimate) |
| Melting Point | 223-226 °C |
| Boling Point | 563.27°C (rough estimate) |
| Specific Rotation(α) | -38.5 º (c=4, H2O) |
| Flash Point | 403.3°C |
| Water Solubility | 83 g/L (25 ºC) |
| Solubility | Easily soluble in boiling water, almost insoluble in ether. |
| Vapor Presure | 3.35E-23mmHg at 25°C |
| Appearance | rorthorhombic columnar crystal |
| Color | White to Off-white |
| Merck | 14,597 |
| BRN | 66856 |
| pKa | 12.69±0.70(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Hygroscopic |
| Refractive Index | -40 ° (C=2, H2O) |
| MDL | MFCD00006598 |
| Physical and Chemical Properties | Dry mature seeds derived from the Rosaceae plant, bitter almond, Northeast China. |
Amygdalin 29883-15-6 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S24/25 - Avoid contact with skin and eyes. |
| UN IDs | 2811 |
| WGK Germany | 3 |
| RTECS | OO8450000 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29389090 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orl-rat: 522 mg/kg WJMDA2 134,97,81 |
Amygdalin 29883-15-6 - Reference
| Reference Show more | 1. Li Ling, Zhang Bo, Lu Fangguo, Cai Liang, Gao Gao Hu Wei, he Guliang, Wu Tao. Effect of influenza A Virus on autophagy of pulmonary macrophages and intervention of maxing Shigan decoction containing serum [J]. Chinese pharmacological Bulletin 2019 35(06):878-884. 2. Liu Ruicheng, Liu Dongke, Li Lian, et al. Simultaneous determination of six effective components in Qilong capsules by HPLC-MS/MS [J]. Journal of Pharmaceutical Analysis 2020v.40(05):36-42. 3. Zhang Huiwen, Liu Guangda, et al. Comparison of HPLC fingerprints of ten almond species [J]. Chinese Journal of Traditional Chinese Medicine, 2018, 36(12):2918-2921. 4. Chen Ming Zhong Zhong Xumei Liu Ping et al. Optimization of debittering technology of fermented plum wine [J]. Food Research and Development, 2017(11):114-118. 5. Xu Zhao, Xiao Xiong, Huang Gang, etc. Material basis and mechanism analysis of ephedra-almond drug pair based on drug-containing intestinal absorption solution [J]. Chinese Journal of Experimental prescriptions, 2018, 024(006):1-6. 6. Liu Ce, 2], Cao Qingming, et al. Determination of amygdalin content in almond skin and study on detoxification technology [J]. Food Research and Development, 2015(3):59-63. 7. Dianxiaokun, Qian Dawei, Duan Jinyan, et al. Comparative study on chemical constituents of peach seed and peach seed [J]. Journal of Pharmaceutical Analysis, 2020, 040(001):123-131. 8. Sun Meng, Ye Liqin, Liu Haijiao, etc. Evaluation of germplasm resources of Prunus humilis [J]. Chinese herbal medicines, 2017, 40(001):54-57. 9. Xie Zhaohui, Li Xin, Li Wenbo, et al. Single factor experiment on extraction of amygdalin from almond by ultrasonic wave [J]. Journal of Henan University of urban construction, 2012, 21(002):31-38. 10. Xie Yu, Zhang Zhi, Li hearing string, etc. Content Comparison of amygdalin in different processed products and their water decoctions of Prunus Aromatica [J]. Chinese Journal of Hospital Pharmacy, 2018(19). 11. Ao Bo, Hou Yongchun, Lai Zhenzhen, etc. Variation of composition-effect of ephedra-almond drug pair [J]. Chinese patent medicine, 2018(6). 12. Yang Li, Li Ying, Wang Qingxian, Sun Yongbing, Liu Wan, Li Wenhong. Study on the ratio of ephedra and almond medicine and the change law of active ingredient content [J]. China Contemporary Medicine, 2017,24(05):4-7 11. 13. Chen Junyi, Jia Tianzhu. Discussion on the significance of stir-frying and processing of bitter almond [J]. Asia-Pacific Traditional Medicine, 2012, 08(006):48-50. 14. Yang Shuang, He Yanqian, Yang Jie, et al. Study on improving the quality standard of cold soft capsules [J]. Shi Zhen, Chinese Traditional Medicine, 2013, 24(008): 530-632. 15. Feng Lunyuan, He Lanping, Li Cuiqin, et al. Screening of microbial β-glucosidase for hydrolyzing ginkgo flavone glycosides from traditional fermented soybean products in Guizhou [J]. Journal of Microbiology, 2020(2). 16. Wan Jianyang, Tian Yanfang, Wan Hai Tong, et al. Pharmacokinetics of Mahuang decoction effective components in Fever rats [J]. Chinese Journal of Traditional Chinese Medicine, 2019, 26 (10). 17. Liu yuembo, Zhang xiaominhong, Bing et al. Comparison of the contents of active ingredients in different preparations of Mahuang decoction and its disassembled prescriptions by HPLC-DAD method [J]. China Science and Technology of traditional Chinese medicine 2020(1). 18. Wang Shiyang, Wang Xiao, Xu Zuqing, Liu Yue, Kong Fanli. Amygdalin attenuates carbon tetrachloride-induced liver fibrosis in rats by inhibiting oxidative stress and inflammation [J]. Modern Immunology, 2020,40(06): 481-475. 19. Xue Mengjie, Yu Xiaojuan, Wang Luyao, Chai Xin, Yang Jing, Wang Yuefei. Study on quantitative variation of components in the extraction process of Xuefu Zhuyu decoction [J]. Tianjin Journal of Traditional Chinese Medicine, 2021,38(01):109-112. 20. Chen kaiqiong, Yang Qifang, Gu Qi, Lv Yan, Liu Jianli. Isolation of lactic acid bacteria from leaves of Lycium barbarum L. And evaluation of its application in silage [J]. China Agricultural Science and Technology Review, 2021,23(02):193-201. 21. Wang Pan, storage root, xuanyun, Cai Zhengyin. Study on fingerprint of didangxianxiong decoction HPLC-MS [J]. Shi Zhen, National Medicine, 2020,31(12):2937-2940. 22. Zhou, Li-Hua, et al. "Label-free quantitative proteomics reveals fibrinopeptide B and heparin cofactor II as potential serum biomarkers in respiratory syncytial virus-infected mice treated with Qingfei oral liquid formula." Chin J Nat Med 16 (2018): 241-25 23. Zhou, Li-Hua, et al." Label-free quantitative proteomics reveals fibrinopeptide B and heparin cofactor II as potential serum biomarkers in respiratory syncytial virus-infected mice treated with Qingfei oral liquid formula." Chin J Nat Med 16 (2018): 241-25 24. Zheng, Mengkai, et al. "Effects of herbal drugs in Mahuang decoction and their main components on intestinal transport characteristics of Ephedra alkaloids evaluated by a Caco-2 cell monolayer model." Journal of ethnopharmacology 164 (2015): 22-29.https:// 25. [IF=3.414] Mengkai Zheng et al."Effects of herbal drugs in Mahuang decoction and their main components on intestinal transport characteristics of Ephedra alkaloids evaluated by a Caco-2 cell monolayer model."J Ethnopharmacol. 2015 Apr;164:22 26. [IF=3.205] Dong-Dong Hu et al."Simultaneous determination of ten compounds in rat plasma by UPLC-MS/MS: Application in the pharmacokinetic study of Ma-Zi-Ren-Wan."J Chromatogr B. 2015 Sep;1000:136 27. [IF=1.773] Li-Hua ZHOU et al."Label-free quantitative proteomics reveals fibrinopeptide B and heparin cofactor II as potential serum biomarkers in respiratory syncytial virus-infected mice treated with Qingfei oral liquid formula."Chin J Nat Medicines. 2018 Apr;16:2 28. [IF=4.225] Wei Wenyang et al."Screening of Antiviral Components of Ma Huang Tang and Investigation on the Ephedra Alkaloids Efficacy on Influenza Virus Type A."Front Pharmacol. 2019 Sep;0:961 29. [IF=3.935] Pengcheng Huang et al."Correlation study between the pharmacokinetics of seven main active ingredients of Mahuang decoction and its pharmacodynamics in asthmatic rats."J Pharmaceut Biomed. 2020 May;183:113144 30. [IF=3] Wan Haoyu et al."Pharmacokinetics of seven major active components of Mahuang decoction in rat blood and brain by LC-MS/MS coupled to microdialysis sampling."N-S Arch Pharmacol. 2020 Aug;393(8):1559-1571 31. [IF=2.193] Zhang Haibo et al.Systematic Study on a Quantitative Analysis of Multicomponents by Single Marker (QAMS) Method for Simultaneous Determination of Eight Constituents in Pneumonia Mixture by UPLC-MS/MS.J Anal Methods Chem. 2021;2021:8311588 32. [IF=1.618] Zhang Guoqin et al."Study on the Correlation Between the Appearance Traits and Intrinsic Chemical Quality of Bitter Almonds Based on Fingerprint-Chemometrics."J Chromatogr Sci. 2022 Apr ;: |
Amygdalin 29883-15-6 - Reference Information
| Introduction | A β-cyanogenic glycoside in bitter almonds, which binds a cyano group (CN) in the molecule. After eating bitter almonds, it will release free Cyano group, so eaters will be poisoned; amygdalin is a product of phenylalanine metabolism in bitter almonds. There are β-glucosidase and almond nitrilase (oxynitrilase) in bitter almonds. The former catalyzes the hydrolysis of amygdalin to two molecules of glucose and one molecule of almond nitrile, and the latter catalyzes the hydrolysis of almond nitrile to cyanide (HCN) and benzaldehyde. Amygdalin is found in seeds, such as almonds. |
| Source | Amygdalin (Amygdalin, from the Greek "almond"), also known as amygdalin, is a toxic cyanide found in many plants, but the most striking is found in the seeds of plants such as apricots, bitter almonds, apples, peaches and plums. Amygdalin is also found in other Prunus plants, including apricots and black cherries, as well as in the leaves, fruits and cores of loquat. |
| Sugars | Many plant root cells contain sugars, which have no toxic effect when they are sugars. Hydrolysis of sugar formulates releases toxic substances, causing cell death. The mandelin contained in peach roots is a sugar ligand. The hydrolysis of mandelin produces two phytotoxins, hydrocyanic acid and benzaldehyde. Peach root lesion formation and necrosis occur in the adjacent parts that are punctured but not contacted by the punctured short-body nematode; and in vitro tests have proved that the punctured short-body nematode can hydrolyze the amygdalin. |
| efficacy and action | almonds contain amygdalin 3%, which is decomposed by enzymes to form hydrocyanic acid. hydrocyanic acid is toxic but a small amount has a sedative effect on the respiratory center. Therefore, it is recorded in the literature that it has the effect of relieving cough and asthma, and has the effect of killing typhoid bacillus and other fungi. In recent years, domestic and foreign scientific research has proved that hydrocyanic acid has anti-cancer effects, which is really a good product for human health. |
| use | as a cyanide containing glucoside, it can be used as a matrix for the identification, differentiation and characterization of maltase, almond cheese and β-glucosidase a cyanide-containing glycoside, which can be used as a substrate to identify, identify and characterize maltase, whey enzyme and β-glucosidase. A cyanide-containing glycoside that can be used as a substrate for identifying, identifying and characterizing enzymes {such as maltase (s), lactase (s) and β-glucosidase s). |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 522 mg/kg; Oral-mouse LD50: 443 mg/kg |
| flammability hazard characteristics | combustible; toxic nitrogen oxide smoke generated by heat |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:04:16
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