Testosterone 睾酮

CAS 58-22-0 MFCD00003654

化学结构图

58-22-0
SMILES: C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O

化学属性

Mol. FormulaC19H28O2
Mol. Weight288.47
Melting Point153-157°C
Density1.12
Stability对光敏感
Appearance D +109°(4%，乙醇)，乙醇溶液在240nm波长处有最大吸收。易溶于乙醇(1：5)和氯仿(1：2)，溶于乙醚(1：100)，不溶于水。LD 24 白色结晶性粉末，无气味。Mp155℃，比旋光度[α] 50 (大鼠，静脉)326 mg/kg。试验表明，对实验动物有潜在的致癌作用。

别名和识别编码

Chemical NameTestosterone
Synonym Percutacrine androgenique 17b-hydroxyandrost-4-ene-3-one Homosterone 17Β-羟雄甾-4-烯-3-酮,17Β-HYDRO TESTOSTERONE 表睾酮 4-ANDROSTEN-17BETA-OL-3-ONE 孕(甾)酮 睾酮-睾丸素 睾酮 溶液 Perandren Testoviron T 17BETA-HYDROXY-3-OXO-4-ANDROSTENE 17BETA-HYDROXY-4-ANDROSTEN-3-ONE and 17-beta-Hydroxy-4-androsten-3-one Virosterone oreton Malestrone (amps) Primotest trans-Testosterone; Androlin; Android; Halotensin; Oreton; Testex; Testoderm; Testred; Virilon; Androst-4-en-17b-ol-3-one; 17b-Hydroxyandrost-4-ene-3-one androlin 17α-羟基雄甾-4-烯 17β-羟基-3-氧代-4-雄甾烯 17β-羟基-4-雄甾烯-3-酮 4-雄甾烯-17β-醇-3-酮 反式-睾酮 Andronaq Synandrol F Andros 睾丸素;17β-羟基-3-氧代-4-雄甾烯;17β-羟基-4-雄甾烯-3-酮;4-雄甾烯-17β-醇-3-酮;反式-睾酮 trans-Testosterone 17-beta-Hydroxy-delta(sup 4)-androsten-3-one 睾酮/5-alpha-Androst-1-烯-3-酮-17-醇 (8R,9S,10R,13S,14S,17S)-17-HYDROXY-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE Teslen 7-beta-Hydroxyandrost-4-en-3-one Cristerone T 睾酮 Geno-cristaux gremy 17-beta-Hydroxyandrost-4-en-3-one PRIMOTESTON Testobase {hazar Orquisteron DELTA-ANDROSTEN-17B-OL-3-ONE {Che 17β-羟基-3-氧代-4-雄甾烯 17β-羟基-4-雄甾烯-3-酮 4-雄 睾丸素 Testryl Testosteroid 睾丸素系列 halotensin Testosteron 睾丸激素 睾酮/5-ALPHA- 4-ANDROSTENE-17BETA-OL-3-ONE HO 17B-HYD
CAS Number58-22-0
PubChem Substance ID6013
EC Number200-370-5
Beilstein Registry Number1915399
MDL NumberMFCD00003654
Chemical Name Translation睾酮
Merck Number13,9255
Wiswesser Line NotationL E5 B666 OV MUTJ A1 E1 FQ
InChIInChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
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分类

  • Androgen, Androgen Modulators, Application Index, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Cell Signaling Enzymes, Cell Signaling and Neuroscience, Cytokines, Growth Factors and Hormones, Enzymes, Inhibitors, and Substrates, Hormones, Steroid Hormones, Substrates, T, Tumor Growth Regulation, Xenobiotics and Drug Metabolism
  • {SA} All Doping Standards (A-Z), Alphabetic, Anabolic Steroide, Analytical Standards, Analytical/Chromatography, Bioactive Small Molecules,
  • {SNA} Analytical Standards,
  • {SNA}
  • {Chemicalbook} 生物化学品: 生化试剂: 激素
  • {SNA} Alphabetical Index of Analytical Standa

产品应用

  • Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.

相关文献及参考

  • Konkle, A.T., and McCarthy, M.M., Developmental Time Course Of Estradiol, Testosterone, And Dihydrotestosterone Levels In Discrete Regions Of Male And Female Rat Brain. Endocrinology 152 , 223-35, (2011) 摘要
  • Merck:13,9255
  • Mainwaring, W.I.P., The mechanism of action of androgens. Monogr. Endocrinol. 10 , 1-178, (1977) 摘要
  • Rosenfield, R. L. Adv. Pediatrics 19 , 172, (1972)
  • Ibebunjo, C., et al., Voluntary Running, Skeletal Muscle Gene Expression, And Signaling Inversely Regulated By Orchidectomy And Testosterone Replacement. Am. J. Physiol. Endocrinol. Metab. 300 , E327-40, (2011) 摘要
  • Merck 14 ,9180
  • Cavaliere, C., et al., Combined Inhibitory Effect Of Formestane And Herceptin On A Subpopulation Of CD44+/CD24low Breast Cancer Cells. Cancer Sci. 101 , 1661-9, (2010) 摘要
  • Merck:13,9255 Beilstein: 8,IV,974

安全信息

GHS Symbol
WGK Germany3
Hazard Codes F,T Xn T T,Xn
Hazard statements
  • H332 Harmful if inhaled 吸入有害
  • H350 May cause cancer 可能致癌
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
RTECSXA3030000
Precautionary statements
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P308+P313
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • 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。
Signal word Danger
Safety Statements
  • 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；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
Risk Statements
  • R11 Highly flammable 非常易燃
  • R20 Harmful by inhalation 吸入有害
  • R19 May form explosive peroxides 可能生成易爆的过氧化物质
  • R45 May cause cancer 可能致癌
  • R60 May impair fertility 可能降低生殖能力
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
Storage condition 2-8°C
UN Number UN 2252 3/PG 2 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Implant
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 400 mg/kg/50D-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Reproductive - Tumorigenic effects - ovarian tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   48,2788,1988

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 30 mg/kg/5D-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Endocrine - adrenal cortex tumors
   Reproductive - Tumorigenic effects - other reproductive system tumors
REFERENCE :
   JNCIAM Journal of the National Cancer Institute.  (Washington, DC)  V.1-60,
   1940-78.  For publisher information, see JJIND8.  Volume(issue)/page/year:
   39,75,1967

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 6240 mg/kg/52D-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Reproductive - Tumorigenic effects - ovarian tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   48,2788,1988

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - species unspecified
DOSE/DURATION           : >5 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TOVEFN Toksikologicheskii Vestnik.  (18-20 Vadkovskii per.  Moscow, 101479,
   Russia) History Unknown  Volume(issue)/page/year: (2),6,1996

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 326 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - other changes
REFERENCE :
   PSEBAA Proceedings of the Society for Experimental Biology and Medicine.
   (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1903/04-
   Volume(issue)/page/year: 46,116,1941

TYPE OF TEST            : Sperm Morphology
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Non-mammalian species
DOSE/DURATION           : 12 mg/8W (Intermittent)
REFERENCE :
   JEZOAO Journal of Experimental Zoology.  (Alan R. Liss, Inc., 41 E. 11th
   St., New York, NY 10003) V.1-    1904-  Volume(issue)/page/year:
   205,403,1978

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Human Kidney
DOSE/DURATION           : 100 ug/L
REFERENCE :
   CNJGA8 Canadian Journal of Genetics and Cytology.  (National Research
   Council of Canada, Publication Sales and Distribution, Ottawa ON K1A OR6,
   Canada)  V.1-    1959-  Volume(issue)/page/year: 10,299,1968

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - mouse Liver
DOSE/DURATION           : 100 umol/L
REFERENCE :
   ENZYAS Enzymologia.  (The Hague, Netherlands)  V.1-43, 1936-72.
   Volume(issue)/page/year: 41,183,1971

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Kidney
DOSE/DURATION           : 100 ug/L
REFERENCE :

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 10 mg/kg
REFERENCE :

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 50 umol/L
REFERENCE :
   PSEBAA Proceedings of the Society for Experimental Biology and Medicine.
   (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1903/04-
   Volume(issue)/page/year: 146,401,1974

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 100 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   45,337,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 20 mg/kg
SEX/DURATION            : female 5 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - pre-implantation mortality (e.g. reduction in
   number of implants per female; total number of implants per corpora lutea)
REFERENCE :
   JOENAK Journal of Endocrinology.  (Biochemical Soc. Book Depot, POB 32,
   Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1939-
   Volume(issue)/page/year: 18,271,1959

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Human - woman
DOSE                    : 34600 ug/kg
SEX/DURATION            : female 7-13 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
   AMDCA5 AMA Journal of Diseases of Children.  (Chicago, IL)  V.91-99,
   1956-60.  For publisher information, see AJDCAI.  Volume(issue)/page/year:
   95,9,1958

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 100 mg/kg
SEX/DURATION            : female 17-20 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
   ECJPAE Endocrinologia Japonica.  (Japan Pub. Trading Co., Ltd., POB 5030,
   Tokyo International, Tokyo, Japan)  V.1-    1954-  Volume(issue)/page/year:
   24,77,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Implant
SPECIES OBSERVED        : Mammal - domestic
DOSE                    : 6491 ug/kg
SEX/DURATION            : female 13-20 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - feta

其他信息

  • 上游原料:二氧化锰 --> 二酮
  • Acros Organics:睾酮/5-alpha-Androst-1-烯-3-酮-17-醇 Testosterone, Eur.Pharm.(58-22-0)
  • 雄性激素:睾酮是睾丸间隙细胞分泌的一
  • 比旋光度:101 ° (c=1, dioxane 25 °C)
  • 睾酮的合成途径:睾丸和卵巢睾酮的合成受黄体生成素的调节，它和间质细胞表面的特异受体结合，通过腺苷酸环化酶(cAMP)系统促进睾酮的合成，其作用的环节是胆固醇转化为20α羟胆固醇的步骤。肾上腺皮质雄激素的合成在网状带进行，受促肾上腺皮质激素的调节。脱氢异雄酮、雄烯二酮入血后，一部分在外周组织转化为睾酮。睾酮的产生率成年男性为每日6～8mg，成年女性为每日0.3mg。 血中的睾酮绝大部分和血浆蛋白相结合。血中的性激素结合球蛋白(SHBG)是一种β球蛋白，分子量52000～115，000，等电点5.5，在60℃即失去活性，它能和睾酮呈特异的结合。结合常数在37℃时为8×108M-1，结合容量在男性为3～5×10-8M，女性为6～7.8×10-8M此蛋白在血中的含量，女性和儿童约比成年男性高一倍。另外，白蛋白、皮质激素结合球蛋白(CBG)，均能和睾酮非特异性地结合。它们的结合常数分别为3.6×104M-1，1.5×106M-1，亲和力远低于性激素结合球蛋白。正常成年男性和SHBG结合的睾酮约占总量的56%和白蛋白结合的约占40%和CBG结合的约占2%，游离的睾酮只有2%，而成年女性则分别为78%、20%、1%、1%。血浆蛋白结合的睾酮可起一种缓冲作用，以维持血中睾酮的浓度在正常生理范围内。游离的睾酮可进入细胞，发挥生理效应，故具生物活性。我国成年男性血浆睾酮水平为360～910ng/dl，平均为570±116ng/dl(±8.0)，女性为21～91ng/d
  • 用途一:生化研究；天然雄性激素，控制男性性器官和男性副性征的发育和生长。
  • Sigma Aldrich:58-22-0(sigmaaldrich)
  • {Chemica
  • 参考质量标准:含量97%-103%；mp152-156℃；比旋光度[α] 20 D +106°-+116°；检测灼烧残渣及干燥失重等杂质含量。
  • 方法一:雄甾-4-烯二酮经氢化锂铝还原，二氧化锰氧化制得。
  • 睾酮价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 164410250 睾酮 Testosterone , Eur.Pharm. 25 GR 2634元 2010/06/21 164410100 睾酮 Testosterone , Eur.Pharm. 10 GR 1251元 2010/06/21 164410050 睾酮 Testosterone , Eur.Pharm. 5 GR 717元
  • 睾酮测定:成年男性血浆中的睾酮，约95%由睾丸分泌，小部分来自肾上腺皮质及腺外转化; 在女性主要来自肾上腺皮质，卵巢也能少量分泌。测定睾酮含量，是直接反映雄性性腺功能的一个有效指标。由于血液中睾酮的含量较低，用一般化学方法很难测定出来。60年代初，曾用气相层析法和双标记核素衍生物法。70年代，采用竞争性蛋白结合法及放射免疫分析法。蛋白竞争结合法是利用人血浆中的性激素结合球蛋白 (SHBG)作为特异试剂，一般采用妊娠末期的孕妇血浆或服避孕药妇女的血浆，因这些血浆中的性激素结合球蛋白的含量较高。放射免疫分析法，是用抗睾酮血清作为特异试剂，取代竞争性蛋白结合法中的性激素结合球蛋白，因而具有更好的特异性和更高的灵敏度。两法的基本原理相同。 主要操作步骤有： 1，样品纯化：一般先用有机溶媒抽提血浆样品中的睾酮，再用层析进行分离。在放射免疫分析法中，如所用抗体特异性很强，层析可以省去; 2，竞争结合反应：在纯化样品中，加入定量放射性核素标记的睾酮 (3H-睾酮)，再加适量的一定稀释度的抗血清或妊娠末期血浆温育一定时间，使样品中睾酮和3H-睾酮与之发生竞争性的结合; 3，分离：以吸附法、沉淀法或固相法等将游离的睾酮(F)和已结合的睾酮(B)分离; 4，测定放射性：取一定量B或F部分，进行计数测量，再对照标准曲线计算样品中睾酮含量。上海市内分泌研究所用放射免疫分析法测定的血浆中睾酮正常值，男性为360～910ng/dl;女性为21～91ng/dl。尿中睾酮排泄量在

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. T - Bioactive Small Molecules
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Others 其他杂环
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. T - Alphabetic
  5. TA - TE - T
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Cytokines, Growth Factors and Hormones - Cell Signaling and Neuroscience
  5. Hormones - Cytokines, Growth Factors and Hormones
  6. Steroid Hormones - Hormones
  7. Androgen - Steroid Hormones
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Steroids
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Xenobiotics and Drug Metabolism
  6. Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Cytokines, Growth Factors and Hormones
  5. Hormones
  6. Steroid Hormones
  7. Aldosterone

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