Gibberellic Acid 赤霉酸

CAS 77-06-5 MFCD00079329

化学结构图

77-06-5
SMILES: C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O

化学属性

Mol. FormulaC19H22O6
Mol. Weight346
Density1.493
Melting Point227
TSCAYes
Solubility5 G/L (20 º C)
Stability对光敏感
Refractive index81 ° (C=2, MeOH)

别名和识别编码

Chemical NameGibberellic Acid
CAS Number77-06-5
Synonym ######## (1A,2B,4aA,4bB,10B)-2,4a,7-trihydroxy-1-methyl-8-methylene-gibb-3-ene-1,10-dicarboxyli (3S,3aR,4S,4aR,7S,9aR,9bR,12S)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,13-propenoazuleno[1,2- 2,4A,7-TRIHYDROXY-1-METHYL-8-METHYLENEGIBB-3-ENE-1,10-DI 2,4A,7-TRIHYDROXY-1-METHYL-8-METHYLENEGIBB-3-ENE-1,10-DIC 2,4a, 7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-carboxylic acid 2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone, Gibberellin A3 2,4a,7-三羟基-1-甲基-8-亚甲基赤霉-3-烯-1,10-二羧酸-1,4a-内酯 Acide gibberel Activol GA GA(3) gibberellin GA3 Gibberellic GA3 赤霉素 A3 GA3 gibberellin GA4 AND 7 GIBBERELIC ACID GIBBERELLIC ACID GA3 Gibberellic acid Gibrescol Grocel Releas
EC Number201-001-0
Beilstein Registry Number54346
MDL NumberMFCD00079329
PubChem Substance ID6466
Merck Number14,4419
Chemical Name Translation赤霉酸
LabNetwork Molecule IDLN00841384
InChIInChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1
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分类

  • {SNA} All alphabetically sorted, Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, Chromatography, E-G, Environmental Standards, G, Pesticides, Pesticides & Metabolites, Plant growth regulators
  • {SNA} Analytical Standards, E-G, 农残和代谢标准品, 分析/色谱, 按照字母排序
  • {SNA} Building Blocks, C13 to C42+, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis, Organic Building Blocks
  • {SNA} Allium sativum (Garlic), Miscellaneous Plant Growth Regulators,
  • {SNA} Allium sativum (Garlic), Phytochemicals by Plant (Food/Spice/Herb), 细胞生物学,

产品应用

  • 赤霉素为植物生长调节剂，主要用于促进作物的生长发育，提早成熟，提高产量和打破种子、块茎、鳞茎等器官的休眠，促进发芽、分蘖、抽苔，提高果实结果率，特别对解决杂交水稻制种中花期不遇有特别功效，在棉花、葡萄、马铃薯、水果、蔬菜上广泛应用。

相关文献及参考

  • Plant growth regulator. For an overview of the chemistry of gibberelins, see: Chem. Rev., 92, 573 (1992).
  • Short: III/5b
  • Short: EINECS
  • Merck: 14,4419
  • Bayle, J. et al.: Chem. Biol., 13, 99 (2006); Ihara, S. et al.: J. Cell Sci., 119, 500 (2006); Suh, B. et al.: Science, 314, 1454 (2006); Rinaudo, K. et al.: Nat. Biotechnol., 25, 795 (2007);
  • Merck: 14,4419 Beilstein: 18,V,9,269

安全信息

Signal word Warning
GHS Symbol
WGK Germany2
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R36 Irritating to eyes 刺激眼睛
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。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • 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
  • P337+P313
RTECSLY8990000
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Hazard Codes Xi
Storage condition 0-6°C 贮存于低温、干燥、避光处。 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 142 gm/kg/78W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Liver - tumors
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: PB223-159

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Amphibian - toad
DOSE/DURATION           : 13200 mg/kg/22W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Liver - tumors
REFERENCE :
   ONCOBS Oncology.  (S. Karger AG, Postfach CH-4009 Basel, Switzerland) V.21- 
     1967-  Volume(issue)/page/year: 45,61,1988

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 8500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YKYUA6 Yakkyoku.  Pharmacy.  (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo,
   Japan)  V.1-    1950-  Volume(issue)/page/year: 30,623,1979

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FMCHA2 Farm Chemicals Handbook.  (Meister Pub., 37841 Euclid Ave.,
   Willoughy, OH 44094)  Volume(issue)/page/year: -,C268,1991

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 6300 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85ARAE "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson
   Publications, 1976/77 revision  Volume(issue)/page/year: 3,43,1976/1977

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   PYTCAS Phytochemistry.  An International Journal of Plant Biochemistry.
   (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1-
      1961-  Volume(issue)/page/year: 11,3135,1972

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Fish - salmon Sperm
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   PYTCAS Phytochemistry.  An International Journal of Plant Biochemistry.
   (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1-
      1961-  Volume(issue)/page/year: 11,3135,1972

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 3 mmol/L
REFERENCE :
   BZARAZ Biologicheskii Zhurnal Armenii.  Biological Journal of Armenia. (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.19-    1966-
   Volume(issue)/page/year: 40,153,1987

其他信息

  • 发现历史:1926年日本病理学家黑泽英一在研究水稻恶苗病时，发现患恶苗病水稻的徒长是由病菌分泌的物质引起的，这种病菌叫赤霉菌。1938年日本薮田贞次郎等从水稻赤霉菌中分离出一种活性制品。并得到结晶，定名为赤霉素(GA)。第一种被分离鉴定的赤霉素称为赤霉酸(GA3)，现已分离和鉴定的赤霉素有70余种，表示其中40多种存在于高等植物中，分别以GA1、GA2，GA3……，使用最广和研究最多的是赤霉酸(GA3)，生产上用得多的还有赤霉素4(GA4)和赤霉素7(GA7)。50年代，美国阿博特实验室(Abbott labora-tories)、英国帝国化学公司(ICI)和日本协和发酵、明治制药等先后投产。1958年中国科学院、北京农业大学亦投入生产。赤霉酸纯品为白色结晶，难溶于水，易溶于乙醇、丙酮和酯类。植物体各组织器官都含赤霉素，合成部位一般在幼芽、幼根、未成熟的种子和胚等幼嫩组织。 图1为赤霉酸(GA3)的结构式。
  • MOL 文件:77-06-5.mol
  • RTECS号:LY8990000
  • 生理效应:赤霉素中生理活性较强、研究最多的是GA3，它能显著地促进植物茎、叶生长，特别是对遗传型及生理型的矮生植物有明显的促进生长的效应。GA3能替代某些种子萌发所需要的光照和低温条件，从而促进发芽。可使长日植物在短日条件下开花，缩短生活周期。GA3能诱导裸子植物中许多杉科、柏科植物的花芽形成;GA4+7则对诱导松科植物的开花有一定效果。GA3具有使瓜类增加雄花数，诱导单性结实，提高坐果率，促进果实生长
  • 生产方法:主要原料为淀粉、花生饼、玉米浆、葡萄糖等，通过生物合成方法制得。赤霉素菌种先经斜面菌种培养（27℃，4～5d)，再经茄子瓶菌种培养（27℃，4～5d)。在种子罐发酵的工艺条件为27℃，72h。发酵罐合成的工艺条件为27℃，160h，生物合成毕经过滤浓缩却得赤霉素成品（浓缩水剂）。 我国农村也采用农副产品如山芋、小麦、玉米、米饭或麦皮等培养菌种（恶苗菌）进行发酵制备赤霉素。 美国哈佛大学一个研究组已完成了赤霉素的人工合成，参见J.Am.Chem.Soc.,1978,1010:8034。
  • 鉴别试验:取试样数毫克溶于硫酸2ml中，应产生带有绿色荧光的红色溶液。
  • 海关编码:29322980
  • 赤霉素价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 69011631 赤霉素（+4℃） 1g 19.8元 2010/06/21 410920250 赤霉素 Gibberellic acid , in dibasic ammonium phosphate 25 GR 3396元 2010/06/21 41091
  • EPA化学物质信息:Gibb-3-ene-1,10- dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl- 8-methylene-, 1,4a-lactone, (1.al
  • NIST化学物质信息:Gibberellic aci
  • 参考质量标准二:含
  • 易溶于醇类、丙酮、乙酸乙酯、碳酸氢钠溶液及pH6.2的磷酸缓冲液，难溶于水和乙醚。水溶液呈酸性，不稳定易失效。遇碱易分解。遇硫酸呈深红色。
  • 含量分析:标准液的制备 准确称取一定量的参比标准赤霉酸(FCC)，其量相当于纯赤霉酸约25mg，放人一50ml容量瓶中，用甲醇溶解并定容后混匀。取此液10.0ml，放人第二只50ml容量瓶，再用甲醇定容并混匀。 试样液的制备准确称取试样约40mg，放人一50ml容量瓶，用甲醇溶解并定容后混匀。取此溶液10.0ml放入一100ml容量瓶中，再用甲醇定容并混匀。 操作 取试样液5.0ml，放入一25mm×200mm具玻塞试管中，另取标准液4.0ml和5.0ml，分别放人同样的试管中。将各试管放入一沸水浴中蒸发至干，再在90℃烘箱中干燥10min。取出加塞，并冷却至室温。各加80%稀硫酸10.0ml以溶解残渣，在沸水浴中加热10rnin，然后在10℃水浴中冷却5min。将各溶液盛于1cm吸收池中，用适当的分光光度计测定这些溶液在波长535nm处的吸光度，用稀硫酸作空白。 将试样液的吸光度记作A u ，记下由4.0ml和5.0ml标准液所测得的吸光度，并从中选择与试样液的吸光度相接近者记作A s ；同时记下该标

系列性分类

  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Plant (Food/Spice/Herb) - Nutrition Research
  4. Allium sativum (Garlic) - Phytochemicals by Plant (Food/Spice/Herb)
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. G - Alphabetic
  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. Pyrroles 吡咯
  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. Pyrroles 吡咯
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Environmental Standards - Chromatography
  5. Pesticides & Metabolites - Environmental Standards
  6. Pesticides - Pesticides & Metabolites
  7. Plant growth regulators - Pesticides
  1. Life Science 生命科学
  2. Plant Biotechnology 植物生物技术
  3. Plant Tissue Culture - Plant Biotechnology
  4. Plant Growth Regulators - Plant Tissue Culture
  5. Miscellaneous Plant Growth Regulators - Plant Growth Regulators
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Plant Growth Regulators
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Molecular Biology
  4. Plant Growth Regulators
  5. Cytokinins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Plant Biotechnology
  4. Plant Tissue Culture
  5. Plant Growth Regulators
  6. Cytokinins