Citrinin 桔霉素/桔青霉素

CAS 518-75-2 MFCD00006912

化学结构图

518-75-2
SMILES: CC1=C2C(=COC(C)C2C)C(=O)C(C(=O)O)=C1O

化学属性

Mol. FormulaC13H14O5
Mol. Weight250
Density1.37
Melting Point175°C (dec.)

别名和识别编码

Chemical NameCitrinin, 98%
CAS Number518-75-2
Synonym (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic Acid (3R,4S)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyra (3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-< 4,6-DIHYDRO-8-HYDROXY-3,4,5-TRIMETHYL-6-OXO-3H-2-BENZOPYRAN-7-CARBOXYLIC ACID 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3h-2-benzopyran-7-carboxylicaci CIT CITRININ, PENICILLIUM CITRINUM Citriain Citrinin Citrinin from penicillium citrinum NSC 186 citrinin,antimycin {} {} {Chem 桔霉素 桔霉素 溶液
PubChem Substance ID54680783
EC Number208-257-2
Beilstein Registry Number5282243
MDL NumberMFCD00006912
Chemical Name Translation桔霉素/桔青霉素
Merck Number13,2351
Wiswesser Line NotationT66 CO HV AUT&J D1 E1 G1 IVQ JQ
LabNetwork Molecule IDLN01265370
InChIInChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,14H,1-3H3,(H,16,17)/t5-,7-/m1/s1
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分类

  • {SNA} Arachidonic Acid Cascade, Hordeum vulgare (Barley), Leukotrienes, Lipids in Cell Signaling, Phytochemicals by Plant (Food/Spice/Herb), 细胞信号转导和神经科学, 细胞生物学, 营养研究
  • {SNA} Arachidonic Acid Cascade, Cell Signaling and Neuroscience, Hordeum vulgare (Barley), Leukotrienes, Lipids in Cell Signaling, Nutrition Research, Phytochemicals by Plant (Food/Spice/Herb), 细胞生物学
  • {SNA} All alphabetically sorted, Analytical Standards, Analytical/Chromatography, Biotoxins, Chromatography, Life Sciences Standards, Mycotoxins, Single component solutions
  • Arachidonic Acid Cascade, Ce

产品应用

  • 一种真菌毒素,发现于谷物和使动物肾中毒的饲料中,是啮齿类动物的制畸剂,该毒素能减少胚泡细胞数量、胚胎存活率、减轻新生儿体重及增加致命的畸形。在培养基中对细胞的毒性和活性氧的类别有关。激活线粒体的凋亡路径,阻碍抗凋亡磷酸化路径。

相关文献及参考

  • Ciegler, A., et al.: Appl. Microbiol., 26, 271 (1973),
  • Creppy, E., et al.: Toxicol. Lett., 28, 29 (1985),
  • DeGroene, E., et al.: Cancer Res., 56, 299 (1996),
  • Merck 14 ,2327
  • Short: III/10a Title: Structure Data of Organic Crystals: C ... C 15 Author: Schudt-Weitz, G.; Strell, I. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: III/10a Year: 1985 ISBN: 3-540-07834-7 ISBN: 978-3-540-07834-0 Internet Resource: DOI:10.1007/b19984 RefComment: XXII, 634 pages. Hardcover Abstract: The volume includes an alphabetical index of all substances and a separate "ring index" with all cyclic compounds.
  • Short: III/35E Title: Nuclear Magnetic Resonance (NMR) Data: Chemical Shifts for Oxygen-17 Author: Duddeck, H.; Toth, G.; Simon, A. Editor: Gupta, R.R.; Lechner, M.D. Source: Landolt-Börnstein, New Series Volume: III/35E Year: 2002 Keyword: Alipathic and Aromatic hydrocarbons; Coupling constant j; Nuclear Magnetic Resonance; chemical shifts δ ISBN: 3-540-42501-2 ISBN: 978-3-540-42501-4 Internet Resource: DOI:10.1007/b92953 RefComment: VII, 230 pages. With CD-ROM., Hardcover Abstract: This volume provides a comprehensive and evaluated compilation of nuclear magnetic resonance data. Chemical shifts and coupling constants of boron-11 and phosphorus-31 (subvol. A), fluorine-19 and nitrogen-15 (subvol. B), hydrogen-1 (subvol. C), carbon-13 (subvol. D), and oxygen-17 (subvol. E) compounds are tabulated together with the gross- and structure formulas and the most readily available solvents. Due to the large amount of the data merely chemical shifts are presented in the printed versions, and all the data, chemical shifts and coupling constants are provided on CD-ROM's.
  • Short: III/5a Title: Structure Data of Organic Crystals: C ... C 13 Author: Schudt, E.; Weitz, G. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: III/5a

安全信息

GHS Symbol
WGK Germany3
Hazard Codes 6.1 F,Xn T
Hazard statements
  • H351 Suspected of causing cancer 怀疑致癌
  • H331 Toxic if inhaled 吸入中毒
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H301 Toxic if swallowed 吞食有毒
  • H332 Harmful if inhaled 吸入有害
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H312 Harmful in contact with skin 皮肤接触有害
  • H302 Harmful if swallowed 吞食有害
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSDJ2275000
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • 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。
  • P301+P310
  • P302+P350
  • P302+P352
  • P304+P340
  • P305+P351+P338
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
Signal word Danger
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S22 Do not breathe dust 不要吸入粉尘;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • 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);
Risk Statements
  • R11 Highly flammable 非常易燃
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入,皮肤接触及吞食都有毒
  • R36 Irritating to eyes 刺激眼睛
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Packing GroupII
UN Number 2811 UN 3462 6.1/PG 3
Hazard Class6.1(a)
Storage condition 储存温度 2-8°C 2-8°C
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 25200 mg/kg/60W-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1975- Volume(issue)/page/year:
   17,281,1983

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 13 gm/kg/32W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   FGIGDO Fujita Gakuen Igakkaishi.  Journal of the Fujita Gakuen Medical
   Society.  (Nagoya Hoken Eisei Daigaku Fujita Gakuen Igakkai, 1-98 Dengakuga,
   Kubo, Kutsukake-Cho, Toyoake, Aichi-Ken 470-11, Japan)  V.1- 1977- 
   Volume(issue)/page/year: 5,77,1981

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

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 35 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - respiratory stimulation
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 88,173,1946

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 50 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Kidney, Ureter, Bladder - changes in tubules (including acute renal failure,
   acute tubular necrosis)
REFERENCE :
   FCTOD7 Food and Chemical Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.20-    1982- Volume(issue)/page/year:
   21,487,1983

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - hamster
DOSE/DURATION           : 66 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 16,355,1978

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 73 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher inf

TYPE OF TEST

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 200 mg/L
REFERENCE :
   FOBLAN Folia Biologica (Prague).  (Academic Press Inc. Ltd., 24-28 Oval Rd.,
   London NW1 7DX, UK) V.1-    1955-  Volume(issue)/page/year: 32,128,1986

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human HeLa cell
DOSE/DURATION           : 300 umol/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 13,2389,1992

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 100 mg/L
REFERENCE :
   FOBLAN Folia Biologica (Prague).  (Academic Press Inc. Ltd., 24-28 Oval Rd.,
   London NW1 7DX, UK) V.1-    1955-  Volume(issue)/page/year: 32,128,1986

TYPE OF TEST            : DNA repair
TEST SYSTEM             : Bacteria - Bacillus subtilis
DOSE/DURATION           : 20 ug/disc
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   36,445,1976

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 100 mg/L
REFERENCE :
   AEMIDF Applied and Environmental Microbiology.  (American Soc. for
   Microbiology, 1913 I St., NW, Washington, DC 20006)  V.31-    1976-
   Volume(issue)/page/year: 52,1273,1986

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 300 mg/L
REFERENCE :
   AEMIDF Applied and Environmental Microbiology.  (American Soc. for
   Microbiology, 1913 I St., NW, Washington, DC 20006)  V.31-    1976-
   Volume(issue)/page/year: 52,1273,1986

TYPE OF TEST

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 30 mg/kg
SEX/DURATION            : female 10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 14,175,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 35 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 30 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   JTEHD6 Journal of Toxicology and Environmental Health.  (Hemisphere Pub.,
   1025 Vermont Ave., NW, Washington, DC 20005)  V.1-    1975/76-
   Volume(issue)/page/year: 13,553,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 20 mg/kg
SEX/DURATION            : female 10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   85EGD4 "Toxins: Animal, Plant and Microbial; Proceedings of the
   International Symposium," Rosenberg, P., ed., New York, Pergamon Press Inc.,
   1978  Volume(issue)/page/year: -,739,1978

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUT

其他信息

  • 类别:有毒物质
  • Sigma Aldrich:518-75-2(sigmaaldrich)
  • 毒性分级:高毒
  • MOL 文件:518-75-2.mol
  • 图谱信息:桔霉素(518-75-2)红外图谱(IR1) 桔霉素(518-75-2)质谱(MS) 桔霉素(518-75-2)红外图谱(IR2)
  • 灭火剂:水, 二氧化碳, 干粉, 砂土
  • 急性毒性:腹腔-大鼠 LD50: 50 毫克/公斤; 腹腔-小鼠 LD50: 35 毫克/公斤
  • 用途一:一种真菌毒素,发现于谷物和使动物肾中毒的饲料中,是啮齿类动物的制畸剂,该毒素能减少胚泡细胞数量、胚胎存活率、减轻新生儿体重及增加致命的畸形。在培养基中对细胞的毒性和活性氧的类别有关。激活线粒体的凋亡路径,阻碍抗凋亡磷酸化路径。
  • 储运特性:库房低温, 通风, 干燥; 与食品原料分开存放
  • 桔霉素价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 229580050 桔霉素 Citrinin 98% 5 MG 1691元
  • Acros Organics:桔霉素 Citrinin, 98%(518-75-2)
  • 可燃性危险特性:可燃, 燃烧时分解有毒氮氧化物, 氯化物气体

系列性分类


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