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腺嘌呤

腺嘌呤用途

Adenine是嘌呤衍生物,为抗代谢类核苷类似物。

腺嘌呤名称

[ CAS 号 ]:
73-24-5

[ 中文名 ]:
腺嘌呤

[ 英文名 ]:
Adenine

[中文别名 ]:

[英文别名 ]:

7(9)H-purin-6-ylamine
Ade
1H-Purine-6-amine
1H-Purine, 6-amino-
Vitamin- B4
Adenin
1,9-Dihydro-6H-purin-6-imine
9H-Purine-6-amine
EINECS 200-796-1
adensoine

腺嘌呤生物活性

[ 描述 ]:

Adenine是嘌呤衍生物,为抗代谢类核苷类似物。

[ 相关类别 ]:

信号通路 >> 细胞周期/DNA损伤 >> DNA/RNA合成

天然产物 >> 糖和糖苷

研究领域 >> 癌症

[ 靶点 ]

Human Endogenous Metabolite

[参考文献]

[1]. Reader V. The assay of vitamin B(4). Biochem J. 1930;24(6):1827-31.

[2]. ORO J, et al. Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide. Arch Biochem Biophys. 1961 Aug;94:217-27.

[相关活性小分子]

腺嘌呤物理化学性质

[ 密度 ]:
1.9±0.1 g/cm3

[ 沸点 ]:
243.2±50.0 °C at 760 mmHg

[ 熔点 ]:
360-365ºC

[ 分子式 ]:
C₅H₅N₅

[ 分子量 ]:
135.127

[ 闪点 ]:
100.9±30.1 °C

[ 精确质量 ]:
135.054489

[ PSA ]:
80.48000

[ LogP ]:
-2.12

[ 外观性状 ]:
白色至灰白色结晶粉末

[ 蒸汽压 ]:
0.0±0.5 mmHg at 25°C

[ 折射率 ]:
1.954

[ 储存条件 ]:
库房通风低温干燥,与食品原料分开存放

[ 水溶解性 ]:
0.5 g/L (20 ºC)

腺嘌呤MSDS

腺嘌呤毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU6125000

CHEMICAL NAME :: Adenine

CAS REGISTRY NUMBER :: 73-24-5

LAST UPDATED :: 199701

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C5-H5-N5

MOLECULAR WEIGHT :: 135.15

WISWESSER LINE NOTATION :: T56 BM DN FN HNJ IZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 227 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 198 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - muscle weakness Lungs, Thorax, or Respiration - cyanosis

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 783 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 70 mg/kg/36D-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9450 mg/kg/6W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 mg/kg/4D-I

TOXIC EFFECTS :: Gastrointestinal - peritonitis Kidney, Ureter, Bladder - other changes Blood - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 525 mg/kg/3W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5040 mg/kg

SEX/DURATION :: male 4 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 200 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 200 mg/kg

SEX/DURATION :: female 10 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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 200 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - gastrointestinal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 500 mg/kg

SEX/DURATION :: male 5 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg/5D (Continuous)

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 200,249,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3548 No. of Facilities: 269 (estimated) No. of Industries: 3 No. of Occupations: 6 No. of Employees: 1284 (estimated) No. of Female Employees: 932 (estimated)

腺嘌呤安全信息

[ 符号 ]:

GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301

[ 警示性声明 ]:
P301 + P310

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
S26-S36

[ 危险品运输编码 ]:
UN 2811 6.1/PG 3

[ WGK德国 ]:
3

[ RTECS号 ]:
AU6125000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1

[ 海关编码 ]:
2936290090

腺嘌呤合成路线

腺嘌呤上下游产品

腺嘌呤上游产品

腺嘌呤下游产品

腺嘌呤制备

4,6-二氯-5-硝基嘧啶用氨水氨化得4,6-二氨基-5-硝基嘧啶，再与甲酸、甲酰氨和硫代硫酸钠一起环合而得。工艺过程如下：将4,6-二氯-5-硝基嘧啶溶解于乙醇，加热至75-78℃回流0.5h，加入氨水，再升温回流1.5h。冷却过滤，水洗，干燥，得4,6-二氨基-5-硝基嘧啶(氨化物)。将甲酰胺、水、氨化物加入反应罐。升温至100-130℃，分次加入保险粉。加毕，降温至100℃，加甲酸，然后升温到170℃，保温2h。减压蒸馏回收溶剂。蒸毕，趁热加水溶解，加活性炭脱色2次。用氨水调节pH8-9，冷却，析出浅黄色固体，过滤，用水洗至无硫酸根。干燥，得腺嘌呤。腺嘌呤也可作为谷氨酸发酵过程的副产品回收得到。工业品为微黄色结晶。

方法一、以次黄嘌呤为原料的合成法
6-氯嘌呤的制备次黄嘌呤精品24g，二甲基苯胺80ml及三氯氧化磷300ml，150℃油浴，回流50min，换水浴加热至70-80℃，真空浓缩至蒸不出为止。浓缩液倒人300g冰块中，剧烈搅拌至全溶，用10mol/L氢氧化钠液中和至 pH 11-12，用甲苯提取至甲苯层无色，中途用10mol/L氢氧化钠调节水层pH值保持pH11-12。冷却，用浓盐酸酸化水层至pH1-2，加氯化钠70g，使之饱和，冰箱冷却24h，过滤，用少量冰水冲洗滤渣，再以8-10倍热水溶解，加活性炭4g脱色(活性炭用无水乙醇200ml洗脱，浓缩，回收部分产品)，趁热过滤，滤液冷却结晶。再用12倍量蒸馏水重结晶，100℃烘干，得6-氯嘌呤8.5-9g。
次黄嘌呤[三氯氧磷，二甲基苯胺]→[150℃, 5min]6-氯嘌呤
6-羟胺嘌吟的制备盐酸羟胺19.74g溶于无水乙醇中，加氢氧化钾18.69g，加热回流15 min，将冷却生成的氯化钾沉淀过滤并用无水乙醇洗涤，合并滤液及洗液，得中性澄清溶液。加入6-氯嘌呤，水浴回流6h后室温过夜，将析出的6-羟胺嘌呤过滤，依次用水及无水乙醇洗涤，干燥器干燥，得产品8.8g，mp 245-251℃。
6-氯嘌呤[盐酸羟胺，氢氧化钾，无水乙醇]→[pH7, 6h]6-羟胺嘌呤
6-氨基嘌呤磷酸盐的制备 6-羟胺嘌呤5g，加水80ml，用10%氢氧化钠溶液调pH值至9，90℃搅拌下分批加入工业用保险粉20g，并保持pH 9，搅拌1h反应至溶液澄清，冷却，室温放置过夜，过滤，水洗滤饼，100℃干燥，得6-氨基嘌呤1.75g。取6-氨基嘌呤4.05g加蒸馏水100ml，磷酸4.2g，加热溶解，浓缩，过滤，无水乙醇洗涤，真空干燥，得6-氨基嘌呤磷酸盐6.3g。
6-羟胺嘌呤[连二亚硫酸钠，氢氧化钠]→[pH9,90℃,1h]6-氨基嘌呤[磷酸]→6-氨基嘌呤磷酸盐
方法二、以丙二酸二乙酯为原料的合成法
4，6-二羟基嘧啶的制备投料比(质量比)为乙醇钠：甲酰胺：丙二酸二乙酯=7：2.13：1。
$乙醇钠先加入反应器中，再加入甲酰胺，加热至30℃加丙二酸二乙酯，加热至75-80℃使有馏分蒸出，快干时换减压蒸馏装置浓缩至干，加水溶解，冷却，盐酸酸化至pH 4，冷却过滤，冰水洗涤，烘干，得黄色产品。
丙二酸二乙酯[甲酰胺，乙醇钠]→[30℃; 74-81℃, pH4]4.6-二羟基嘧啶
4, 6-二羟基-5-硝基嘧啶的制备将100ml硝酸冷却，搅拌下加入浓硫酸36ml，冷至30℃后分次加入4，6-二羟基嘧啶48g，加料时保持内温为30-35℃，加完后水浴加热至37-40℃搅拌反应1.5h，将反应液倾人25g碎冰中，放置，过滤，冰水洗涤至中性，抽滤烘干得淡黄色产品。
4, 6-二羟基嘧啶[硝酸，硫酸]→[37-40℃,1.5h]4, 6-二羟基-5-硝基嘧啶
4，6-二氯-5-硝基嘧啶的制备三氯氧磷120ml，搅拌下加入4，6-二氨基-5-硝基嘧啶60g，加热至50℃，滴加二甲基苯胺，滴完后回流反应1h，将反应液倾入900g碎冰中，放置至冰块全部溶解，过滤，冰水洗涤，得淡黄色产品。
4, 6-二羟基-5-硝基嘧啶[三氯氧磷，二甲基苯胺]→4, 6-二氯-5-硝基嘧啶
4，6-二氨基-5-硝基嘧啶的制备将4，6-二氯-5-硝基嘧啶用300ml乙醇溶解，水浴缓慢回流并缓慢滴加氨水400ml，滴加时保持温度65℃左右，加完后继续回流1.5h，冷却放置过夜后过滤，冰水洗涤干燥得棕色产品。4, 6-二氯-5-硝基嘧啶[乙醇，氨水]→4,6-二氨基-5-硝基嘧啶
6-氨基嘌呤磷酸盐的制备甲酰胺200ml，搅拌下加入4，6-二氨基-5-硝基嘧啶26g和甲酸30ml，升温至110℃后分次加入保险粉25g，并控制内温为110-120℃，加完后升温至180-190℃，反应2.5h，冷却过夜后抽滤分别用乙醇和冰水洗涤至中性，再用600ml蒸馏水重结晶，抽滤烘干得淡黄色6-氨基嘌呤。加蒸馏水250ml，加磷酸0.0125g，调节pH为1-2，加热，活性炭脱色，趁热抽滤，滤液冷却后抽滤，干燥得产品。
4, 6-二氨基-5-硝基嘧啶[甲醇，甲酰胺，连二亚硫酸钠]→6-氨基嘌呤[磷酸]→6-氨基嘌呤磷酸盐。

腺嘌呤海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

腺嘌呤文献

Multifactorial analysis of conditional reprogramming of human keratinocytes.

PLoS ONE 10(2) , e0116755, (2015)

Co-culture of human primary epithelial cells with irradiated 3T3 fibroblast feeder cells (J2 cells) and the Rho kinase inhibitor Y-27632 (Y) allows for the unrestricted growth of cells of epithelial o...

Vegetables' juice influences polyol pathway by multiple mechanisms in favour of reducing development of oxidative stress and resultant diabetic complications.

Pharmacogn. Mag. 10(Suppl 2) , S383-91, (2014)

Hyperglycemia induced generation of free radicals and consequent development of oxidative stress by polyol pathway is one of the crucial mechanisms stirring up development of diabetic complications. W...

Dynamic switching of active promoter and enhancer domains regulates Tet1 and Tet2 expression during cell state transitions between pluripotency and differentiation.

Mol. Cell. Biol. 35(6) , 1026-42, (2015)

The Tet 5-methylcytosine dioxygenases catalyze DNA demethylation by producing 5-hydroxymethylcytosine and further oxidized products. Tet1 and Tet2 are highly expressed in mouse pluripotent cells and d...

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腺嘌呤