1000μg/mL咖啡因-甲醇溶液(GBW(E)100174)) 咖啡因(精神管制，不能销售）
CAS 58-08-2 MFCD00005758
化学结构图
SMILES: Cn1c(=O)c2c(ncn2C)n(C)c1=O
化学属性
| Mol. Formula | C8H10N4O2 |
|---|---|
| Mol. Weight | 194.22 |
| Melting Point | 234-236.5 °C(lit.) |
| Density | 1.23 |
| Solubility | Soluble in pyrrole, THF-H2O mixture, ethyl acetate |
| TSCA | Yes |
| Boiling Point | 178° subl. |
| Flash Point | 178°C |
| Appearance | 18 4 (大鼠、经口) 260mg/kg。 白色柔韧有弱光的针状结晶，无臭，味苦。露置干燥空气中可风化，80℃全部失水，178℃升华。Mp235-237.5C，相对密度(d )1.23。本品溶于氯仿(1：7)、水(1：60)、乙醇(1：130)，易溶于稀酸，微溶于乙醚。水溶液对石蕊呈中性，与有机酸或其碱金属盐如苯甲酸钠、水杨酸钠、枸橼酸钠或桂皮酸钠等形成复盐，可加大水中的溶解度。中等毒，LD 50 |
别名和识别编码
| Chemical Name | 1000μg/mL咖啡因-甲醇溶液(GBW(E)100174)) |
|---|---|
| Synonym | 咖啡因, 99.7% Methyltheobromide Caffeine Hydrate Coffeine Thein 1,3,7-三甲基黄嘌呤,1,3,7- TRIMETHYXATHINE 7-METHYLTHEOBROMINE 咖啡因 ( 精神类不能定购) 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl- 茶素 1,3,7-TRIMETHYLXANTHINE 3,7-二氢-1,3,7-三甲基-1H-嘌呤-2,6-二酮 1,3,7-Trimethyl-2,6-dioxopurine 3,7-DIHYDRO-1,3,7-TRIMETHYL-IH- Kofein 一水咖啡因 Theobromine, 1-methyl- 甲基可可豆碱 COFFEIN GUARANINE 咖啡因 1,3,7-Trimethylxanthine 无水咖啡碱 Organex TIMTEC-BB SBB006474 1,3,7-Trimethyxanthine Eldiatric C COFFEINUM 咖啡鹼 Mettler-Toledo® 校准物质 ME 18872，咖啡因 咖啡因,CAFFEINE COFFEINE Guaranine 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione METHYLTHEOBROMIDE Koffein 3,7-DIHYDRO-1,3,7-TRIMETHYL-1H-PURINE-2,6-DIONE 1,3,7-TRIMETHYLXANTHINE MONOHYDRATE 3,7-Dihydro-1,3,7-trimethyl-1H-purin Coffeinum METHYLTHEOBROMINE Anhydrous caffeine NO-Doz CAFFEINE MONOHYDRATE 咖啡因 ( 精神类不能定购） NCI-C02 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 咖啡因;3,7-二氢-1,3,7-三甲基-1H-嘌呤-2,6-二酮,咖啡碱;无水咖啡因,1,3,7-三甲基黄嘌呤;茶素;无水咖啡碱 1,3,7-三甲黃嘌呤 1,3,7-三甲基-3,7-二氢-1H-嘌呤-2,6-二酮 Caffeina 1,3,7-TRIMETHYL-2,6-DIOXOPURINE Xanthine, 1,3,7-trimethyl FEMA 2224 Theine 1,3,7-TRIMETHYL-3,7-DIHYDRO-PURINE-2,6-DIONE C Caffein |
| CAS Number | 58-08-2 |
| PubChem Substance ID | 2519 |
| EC Number | 200-362-1 |
| Beilstein Registry Number | 0017705 |
| MDL Number | MFCD00005758 |
| Merck Number | 14,1636 |
| Chemical Name Translation | 咖啡因(精神管制，不能销售） |
| Wiswesser Line Notation | T56 BN DN FNVNVJ B1 F1 H1 |
| InChI | InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 |
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分类
- 1694 Pharmaceuticals & Personal Care Products, Alkaloid, Analytical Standards, Analytical/Chromatography, Bioactive Small Molecules, C-CH, Cell Biology, EPA, Method Specific, Neats, Nutrition Research, Phytochemicals by Chemical Classification
- {SNA} A - D, A-D, Alphabetical Listings, C-D, Flavors and Fragrances, Halal Certified Products, Kosher Certified Products
- {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, Bioactive Small Molecules, Cell Biology, M,
相关文献及参考
- Hadfield, M.G., Caffeine and the olfactory bulb. Mol. Neurobiol. 15 , 31-39, (1997) 摘要
- Ferre, S., et al., Adenosine-dopamine receptor-receptor interactions as an integrative mechanism in the basal ganglia. Trends Neurosci. 20 , 482-487, (1997) 摘要
- Shafer, S.H., et al., Reduced DNA synthesis and cell viability in small cell lung carcinoma by treatment with cyclic AMP phosphodiesterase inhibitors. Biochem. Pharmacol. 56 , 1229-1236, (1998) 摘要
- Islam, M.S., et al., In situ activation of the type 2 ryanodine receptor in pancreatic beta cells requires cAMP-dependent phosphorylation. Proc. Natl. Acad. Sci. U. S. A. 95 , 6145-6150, (1998) 摘要
- He, A.W., and Cory, J.G., p53-independent anisomycin induced G1 arrest and apoptosis in L1210 cell lines. Anticancer Res. 19 , 421-428, (1999) 摘要
- Poe, B.S., and O'Neill, K.L., Caffeine modulates heat shock induced apoptosis in the human promyelocytic leukemia cell line HL-60. Cancer Lett. 121 , 1-6, (1997) 摘要
- Takagi, M., et al., DNA damage-associated cell cycle and cell death control is differentially modulated by caffeine in clones with p53 mutations. Leukemia 13 , 70-77, (1999) 摘要
- Merck 14 ,1636
- Beil. 26 ,461 / Beil. 26 ,IV,2338
- Aldrich MSDS 1 , 343:A / Corp MSDS 1 (1), 664:C / FT-IR 1 (2), 710:B / FT-IR 2 (3), 3668:B / IR-Spectra (2), 1120:B / IR-Spectra (3), 1287:D / NMR-Reference 2 (2), 586:A / RegBook 1 (2), 2467:A / Sax 6 , 615 / Sigma FT-IR 1 (1), 581:A / Structure Index 1 , 390:E:3
安全信息
GHS Symbol
- H315 Causes skin irritation 会刺激皮肤
- H370 Causes damage to organs 导致器官损伤
- H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
- H301+H311+H331
- H319 Causes serious eye irritation 严重刺激眼睛
- H302 Harmful if swallowed 吞食有害
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P301+P310
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P305+P351+P338
- P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
- P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
- S2 Keep out of the reach of children 避免儿童触及；
- R22 Harmful if swallowed 吞咽有害
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 30800 mg/kg/44W-C TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors Tumorigenic - increased incidence of tumors in susceptible strains REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 48,2078,1988
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 62 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea REFERENCE : TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 29,25,19
TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - cat DOSE/DURATION : 100 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1335,1935
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 251 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 53,2S,1957
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 96 mg/kg/1D-I TOXIC EFFECTS : Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis Gastrointestinal - hypermotility, diarrhea REFERENCE : JOPDAB Journal of Pediatrics. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) V.1- 1932- Volume(issue)/page/year: 105,493,1984
TYPE OF TES
{TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Bacteria - Bacillus subtilis DOSE/DURATION : 2500 mg/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 117,55,1983
TYPE OF TEST : DNA repair TEST SYSTEM : Bacteria - Salmonella typhimurium DOSE/DURATION : 10 pph REFERENCE : AGACBH Agents and Actions, A Swiss Journal of Pharmacology. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1969/70- Volume(issue)/page/year: 4,286,1974
TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Microorganism - not otherwise specified DOSE/DURATION : 5000 ppm REFERENCE : IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 13,387,1975
TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Microorganism - not otherwise specified DOSE/DURATION : 400 mg/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 43,37,1977
TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Bacteria - Klebsiella pneumoniae DOSE/DURATION : 2 gm/L REFERENCE : EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 25,85,1969
TYPE OF TEST : DNA damage ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - mouse DOSE/DURATION : 100 mg/kg REFERENCE : ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE : 1650 mg/kg SEX/DURATION : female 6-16 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 23,57,1982
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE : 42
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE : 350 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 5,3,1985
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE : 400 mg/kg SEX/DURATION : female 13 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - gastrointestinal system REFERENCE : FOMOAJ Folia Morphologica (Warsaw). (Panstwowy Zaklad Wydawnictw Lekarskic
其他信息
- 可燃性危险特性:热分解排出有毒氮氧化物烟雾; 过量服用兴奋, 失眠, 呕吐, 下泻
- 参考质量标准一:I. GB 14758-93@QB 2079-95 (通用标准)@(天然咖啡因) 含量/% 98.5～101.0(干基计) 99.0～101.5 砷 ≤0.0003%(GT-3) ≤0.0001% 重金属 ≤0.001% ≤0.001% 熔程/℃ 235～237.5 235.0～237.0 其他生物碱 无沉淀产生 阴性 易炭化物 正常 比色液D
- 使用限量:GB 2760-96：可乐型饮料0.15g/kg。 FAO/WHO(1984)：200mg/kg。 FDA，§182.1180(2000)：0.02%。 FEMA：饮料120mg/kg。
- 方法一:咖啡因可从茶叶、咖啡豆、可可中提取，但目前主要采用人工合成法生严。 尿素法 氯乙酸用碳酸钠溶液中和至Ph=7.5～8.0，中和液加入氰化钠溶液中，在105～115℃下进行氰化反应2～5min得氰乙酸钠溶液。用盐酸酸化氰乙酸钠溶液，并在60～70℃(23.3kPa)下减压脱去大部分水。冷却后过滤除去析出的氯化钠，滤液继续浓缩至85℃(10.6kPa)，加入回收乙酸，继续蒸酸带水至90℃(6.65kPa)，得含水分低于1％的氰乙酸。 将尿素加入氰乙酸，在75℃下搅拌20min，然后加入乙酐，并在≤98℃下保温30min。反应结束后减压回收乙酸，然后加水溶解，冷却至40℃，过滤、洗涤得氰乙酰脲。将氰乙酰脲加入30℃的氢氧化钠溶液中，在≤60℃下保温2.5h。之后加水溶解，加硫酸酸化，过滤除去硫酸钠后得4-亚氨基脲嘧啶溶液。 将亚硝酸钠加入上述溶液，在16～18℃下缓慢加入硫酸，并在≤40℃下反应至淀粉碘化钾试纸变蓝为止。然后在30℃下加入铁粉，控制温度40～45℃，Ph值3.5～3.8(期间加硫酸调Ph值)。还原结束后升温至60～63℃过滤，滤饼用水洗2次，滤饼加水搅拌，在40～45℃加入甲酸，并加热至100℃，保温酰化2h。冷却后过滤，滤饼用水洗涤，得4-氨基-5-甲酰胺基脲嘧啶。 将30％的氢氧化钠加入4-氨基-5-甲酰胺基脲嘧啶和水混合物，使Ph值为9.6，然后加入硫酸二甲酯进行甲基化，控制温度40～45℃，Ph值9.3～9.6(期间加入氢氧化钠溶液)，加料后保温搅拌30min。用30％的硫酸中和至中性，加入活性炭保温脱色30min。压滤后，滤液冷却结晶得咖啡因粗品，再$经脱色、精制得到成品。二甲脲法 40％的甲胺水溶液在100～110℃下气化后，通入熔融的尿素(≥132℃)缩合得到二甲基脲。将乙氰酸加入熔融的二甲基脲，冷至55～60℃时加入乙酐。缩合反应放热升温至90℃，保温30min后，减压蒸酸。蒸至90～98℃(6.65kPa)时，加水溶解得二甲基氰乙酰脲溶液。 用30％的氢氧化钠溶液调节其Ph值至9.5，并在90℃下环合反应1h。然后加入亚硝酸钠，冷却至30℃后加入30％～35％的硫酸，并在≤45℃下亚硝化反应1h(淀粉碘化钾试液显蓝色为终点)。反应结束后冷至室温，过滤并水洗至中性，得滤饼即为1，3-二甲基-4-亚氨基紫脲酸。 将1，3-二甲基-4-亚氨基紫脲酸、水和铁粉加入反应釜，升温至50℃后分批加入氯化钠，控制还原反应温度85℃，反应后期升温至100℃反应15min。过滤并水洗滤饼，滤液和洗液合并后加入甲酸，在1 00℃下甲酰化20min。冷却后过滤得1，3-二甲基-4-氨基-5-甲酰胺基脲嘧啶和母液。 将水和上述母液加入反应釜，再加入1，3-二甲基-4-氨基-5-甲酰胺基脲嘧啶，加热至95℃并用氢氧化钠溶液调Ph值13～14，环合反应30min。然后在40℃下加入硫酸二甲酯，并控制在Ph值9.3～9.4下甲基化30min。之后用稀硫酸中和至Ph值7.5～8.0，加入活性炭脱色30min。冷却结晶、甩干得咖啡因粗品，精制后得成品。
- 方法三:1.尿素法 由氯乙酸经中和、氰化、酸化得到氰乙酸，然后与尿素缩合得氰乙酰脲，再经环合、酸化、亚硝化、还原、酰化、甲基化得到咖啡因。2.二甲脲法 由尿素和一甲胺缩合成二甲基脲，再与氰乙酸缩合为1，3-二甲基乙酰脲，然后经环合、亚硝化、还原、甲酰化、环合、甲基化而得咖啡因。二甲脲法收率高、成本低、消耗少、周期短、设备要求不高、操作简便、容易控制，适合于工业生产。此外，在生产低含量咖啡因的咖啡时，可得到副产品咖啡因。除了从天然物质提取的方法和上述全合成法外，还有半合成法。人可可提取可可碱，然后甲基化得到咖啡因，这是较早的半合成法。从鸟类粪素或尿酸制备咖啡因也属于这类合成法。
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