B-赤霉醇 | 42422-68-4

• 物质功能分类: 分析化学 - 标准品 - 食品和化妆品标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 中文名称: B-赤霉醇
• 中文别名: B-玉米赤霉醇
• 英文名称: taleranol
• 英文别名: beta-Zearalanol；7-β-hydroxy-zearalanol；β-zearalanone；β-zearalanol；7β-zearanol；(4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-2-one
• CAS: 42422-68-4
• 化学式: C₁₈H₂₆O₅
• 分子量: 322.401
• InChiKey: DWTTZBARDOXEAM-JSGCOSHPSA-N

物化性质

• 熔点：
  134-137°C
• 沸点：
  576.0±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)
• 闪点：
  2℃
• 溶解度：
  甲醇：10mg/mL
• 碰撞截面：
  175.33 Ų [M+H-H2O]+; 180.34 Ų [M+Na]+

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  T,Xn,F
• 安全说明：
  S36/37/39,S45,S53
• 危险类别码：
  R60,R36/37/38
• WGK Germany：
  2,3
• 危险标志：
  GHS07,GHS08
• 危险性描述：
  H315,H319,H335,H360
• 危险性防范说明：
  P201,P261,P305 + P351 + P338,P308 + P313
• 储存条件：
  | -20°C |

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: β-Zearalanol
Product name
CAS-No. : 42422-68-4

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Reproductive toxicity (Category 1B)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
May impair fertility. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
May damage fertility or the unborn child.
Precautionary statement(s)
Obtain special instructions before use.
Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P308 + P313 IF exposed or concerned: Get medical advice/ attention.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R60 May impair fertility.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S53 Avoid exposure - obtain special instructions before use.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Restricted to professional users.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: 2,4-Dihydroxy-6-(6β,10-dihydroxyundecyl]benzoic acid μ-lactone
Synonyms
Formula : C18H26O5
Molecular Weight : 322,4 g/mol
Component Concentration
B-Zearalanol
CAS-No. 42422-68-4 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
Some steroids show carcinogenic and teratogenic activity., To the best of our knowledge, the chemical,
physical, and toxicological properties have not been thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.Avoid exposure - obtain special
instructions before use.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
Some steroids show carcinogenic and teratogenic activity.
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Some steroids show carcinogenic and teratogenic activity.
Presumed human reproductive toxicant
May cause reproductive disorders.
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion
May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes
Causes serious eye irritation.
Signs and Symptoms of Exposure
Some steroids show carcinogenic and teratogenic activity., To the best of our knowledge, the chemical,
physical, and toxicological properties have not been thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

β-玉米赤霉烯醇（β-Zearalanol）是由镰刀菌属产生的一种霉菌毒素，可以在哺乳动物生殖细胞中引起细胞凋亡和氧化应激反应。它是一种玉米赤霉烯酮（ZEA）的衍生物，并可与葡萄糖醛酸结合。

体外研究

在HepG2细胞中，β-玉米赤霉烯醇（0-100 μM；72小时）以剂量依赖性方式表现出高度毒性，半数抑制浓度（IC50）为15.2 μM。同时，在BGC细胞中，β-玉米赤霉烯醇（0-200 μM；24小时）以剂量依赖性方式抑制细胞增殖，半数抑制浓度（IC50）为25 μM。此外，当与ZOL或α-ZOL联用时，表现出协同效应，其半数抑制浓度（IC50）分别为19.8 uM和16.8 uM。

在HepG2细胞中，β-玉米赤霉烯醇（0-10 μM；72小时）对三种研究的细胞因子IL-8、IL-1β和TNF-α抑制效果最强，并且优于ZEA或α-Zearalenol。

细胞活力测定

• 细胞系：HepG2细胞
• 浓度：0-100 μM
• 孵育时间：72小时
• 结果：β-玉米赤霉烯醇处理的细胞显示出剂量依赖性的存活率减少。

细胞增殖测定

• 细胞系：BGC细胞
• 浓度：0 μM, 5 μM, 10 μM, 15 μM, 25 μM, 50 μM, 100 μM, 和 200 μM
• 孵育时间：24小时
• 结果：以剂量依赖性方式抑制细胞增殖。

RT-PCR

• 细胞系：HepG2细胞
• 浓度：1 μM, 5 μM, 10 μM
• 孵育时间：72小时
• 结果：与α-Zearalenol相比，显示出更高的细胞毒性效果。

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 B-赤霉醇 在 Pseudomonas fluorescens 作用下， 以 正庚烷 为溶剂， 生成 6'-Acetyl-beta-zearalanol
  参考文献：
  名称：

  间苯二酸大环内酯衍生的仲醇绝对构象与荧光假单胞菌脂肪酶在有机溶剂中的立体选择性反乙酰化的相关性

  摘要：

  非对映体对的Transacetylation秒。衍生自间苯二酸的大环内酯的醇；7α，β-反式-zearalenols（1，2，全名，（3S，7R和3S，7S）反式- 3,4,5,6,9,10八氢7,14,16三羟基-3-甲基-1H-2- benzoxacyclotetradecine -1-酮），7α，β-顺-zearalenols（5，6），和7α，β-zearanols（9，10，全名。，（3S，7R和3S，7S）乙酸乙烯酯催化3,4,5,6,9,10,11,12-十氢-714,16-三羟基-3-甲基-1H-2-苯并氧杂环十四烷-1-酮）假单胞菌 研究了正庚烷和乙腈中的荧光假单胞菌脂肪酶。它具有很高的立体选择性。非对映体过量的7β-O-乙酸酯通常接近100％。ķ中号，V最大和特异性恒转矩压最大值/ K中号不显著为7β-不同的立体异构体2，6和10。但是，它们在从正庚烷到乙腈的过程中会发

  DOI：

  10.1016/s0040-4020(01)85687-8
• 作为产物：
  描述：

  玉米烯酮 在 sodium tetrahydroborate 、 5 mol% Pd/C 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 B-赤霉醇
  参考文献：
  名称：

  半合成玉米赤霉烯酮类似物的合成和细胞毒活性

  摘要：

  玉米赤霉烯酮是具有多种生物活性的β-间苯二酸大环内酯。本文中，我们报道了34种玉米赤霉烯酮类似物的合成及其对人口腔表皮样癌（KB）和人乳腺腺癌（MCF-7）细胞以及非癌性Vero细胞的杀伤活性。一些玉米赤霉烯酮类似物对两种癌细胞显示出适度增强的细胞毒活性。我们发现了潜在的先导化合物，对Vero细胞的细胞毒性降低或没有。初步的结构-活性关系研究表明，玉米赤霉烯酮核心1'和2'位置的双键对于这两种细胞系的细胞毒活性均至关重要。此外，对于玉米赤霉烯醇类似物，C-2处未保护的羟基和C-4处的烷氧基取代基在两种细胞系的细胞毒性作用中均起关键作用。

  DOI：

  10.1016/j.bmcl.2016.06.007

文献信息

• [EN] A PROCESS FOR MANUFACTURING ZERANOL<br/>[FR] PROCÉDÉ DE FABRICATION DE ZÉRANOL
  申请人：INTERVET INT BV

  公开号：WO2010115478A1

  公开（公告）日：2010-10-14

  This invention is directed generally to a process for producing Zeranol that eliminates high pressure and high temperature hydrogenations and provides high selectivity for Zeranol at improved yields.

  这项发明通常涉及一种生产Zeranol的过程，该过程消除了高压和高温氢化反应，并且在高产率下为Zeranol提供了高选择性。
• Pochonins A−F, New Antiviral and Antiparasitic Resorcylic Acid Lactones from <i>Pochonia </i><i>c</i><i>hlamydosporia </i>var. <i>c</i><i>atenulata</i>
  作者：Veronika Hellwig、Anke Mayer-Bartschmid、Hartwig Müller、Gisela Greif、Gerald Kleymann、Werner Zitzmann、Hans-Volker Tichy、Marc Stadler

  DOI：10.1021/np020556v

  日期：2003.6.1

  isolated from cultures of the clavicipitaceous hyphomycete Pochonia chlamydosporia var. catenulata strain P 0297. Fermentation of P 0297 in bromide-containing culture media led to a shift in secondary metabolite production and yielded monocillins III (3) and II (9) as major metabolites besides monorden (1) as well as the novel compounds pochonin F (10) and a monocillin II glycoside (11) as minor metabolites

  Monorden（1）和新颖的间苯二酸内酯蛋白软骨素A（2），B（4），C（6），D（7）和E（8）以及四氢monorden（5）和假神经素A（22）分别为分离自锁骨次霉菌Pochonia chlamydosporia var的培养物。catenulata菌株P0297。在含溴的培养基中发酵P 0297导致次生代谢产物的转移，并产生了Monocillins III（3）和II（9）作为除monorden（1）以及新型化合物软骨素的主要代谢产物F（10）和Monocillin II糖苷（11）作为次要代谢物。这些化合物中的大多数在针对单纯疱疹病毒1（HSV1）和寄生虫原生动物艾美球虫的细胞复制试验中显示中等活性。与结构相关的玉米赤霉烯酮衍生物相反，菌株P 0297的代谢产物在荧光偏振测定中没有活性，可以测定对人雌激素受体ERbeta的调节活性。β-玉米赤霉烯醇（17），但没有玉米赤霉烯酮（1
• [EN] CARBONATE PRODRUGS AND METHODS OF USING THE SAME<br/>[FR] PROMÉDICAMENTS CARBONATÉS ET LEURS MÉTHODES D'UTILISATION
  申请人：NEUROGESX INC

  公开号：WO2009143297A1

  公开（公告）日：2009-11-26

  The present invention provides carbonate prodrugs which comprise a carbonic phosphoric anhydride prodrug moiety attached to the hydroxyl or carboxyl group of a parent drug moiety. The prodrugs may provide improved physicochemical properties over the parent drug. Also provided are methods of treating a disease or condition that is responsive to the parent drug using the carbonate prodrugs, as well as kits and unit dosages.

  本发明提供了碳酸盐前药，其包括连接到母药基团的羟基或羧基上的碳酸磷酸酐前药基团。这些前药可能比母药具有改进的物理化学性质。还提供了使用碳酸盐前药治疗对母药具有响应的疾病或症状的方法，以及配套工具和单剂量。
• [EN] PRODRUG COMPOSITIONS AND METHODS OF TREATMENT<br/>[FR] COMPOSITIONS DE PROMÉDICAMENT ET PROCÉDÉS DE TRAITEMENT
  申请人：AQUESTIVE THERAPEUTICS INC

  公开号：WO2021087359A1

  公开（公告）日：2021-05-06

  Pharmaceutical compositions include a prodrug of epinephrine are described.

  药物组合物包括表述的肾上腺素前药。
• Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients
  申请人：Rogers D. Robin

  公开号：US20070093462A1

  公开（公告）日：2007-04-26

  Disclosed are ionic liquids and methods of preparing ionic liquid compositions of active pharmaceutical, biological, nutritional, and energetic ingredients. Also disclosed are methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture.

  揭示了离子液体及制备活性药物、生物、营养和能量成分的离子液体组合物的方法。还揭示了利用本文描述的组合物的方法，以克服多型性、克服溶解度和输送问题、控制释放速率、增加功能性、增强功效（协同作用）以及改善易用性和制造工艺。