甲基补骨脂黄酮A | 19879-30-2

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 甲基补骨脂黄酮A
• 中文别名: 补骨脂二氢黄酮甲醚；甲基补骨脂黄酮；补骨脂双氢黄酮甲醚
• 英文名称: -(2-hydroxy-3-methylbutane)-2-(4-hydroxyphenyl)-7-methoxychroman-4-one
• 英文别名: 7-O-methylbavachin；7-methoxy-bavachin；(S)-bavachinin；bavachinin A；bavachinine；bavachinin；(2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• CAS: 19879-30-2
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: VOCGSQHKPZSIKB-FQEVSTJZSA-N

物化性质

• 熔点：
  139-145°C
• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.182
• 溶解度：
  DMF：50mg/mL； DMF:PBS (pH 7.2)(1:3)：0.25 mg/mL；二甲基亚砜：30mg/mL；乙醇：20mg/mL
• LogP：
  3.946 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  N
• 安全说明：
  S61
• 危险类别码：
  R50
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Bavachinin
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 19879-30-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute aquatic toxicity (Category 1), H400
Chronic aquatic toxicity (Category 1), H410
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
N Dangerous for the R50
environment
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P501 Dispose of contents/ container to an approved waste disposal plant.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Molecular Weight : 338,40 g/mol
CAS-No. : 19879-30-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Bavachinin
Aquatic Acute 1; Aquatic -
Chronic 1; H410
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Bavachinin
N, R50 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
Flush eyes with water as a precaution.
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
no data available
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
Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
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 use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

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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 154 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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- log Pow: 4,722
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
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
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
Very toxic to aquatic life with long lasting 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. 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: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Bavachinin)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Bavachinin)
IATA: Environmentally hazardous substance, solid, n.o.s. (Bavachinin)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

补骨脂二氢黄酮甲醚是从中药补骨脂中提取的一种异戊烯基黄酮类化合物，具有抗炎、平喘、抗氧化以及抗肿瘤等多种药理作用，展现出一定的开发前景。

生物活性

Bavachinin（7-O-Methylbavachin）是一种天然化合物，具备抗炎症和抗血管生成活性。

靶点

• PPARγ (细胞自由测定)：223 nM (Ki)
• PPAR-β/δ (细胞自由测定)：5.275 μM (Ki)
• PPARα (细胞自由测定)：7.881 μM (Ki)

化学性质

补骨脂二氢黄酮甲醚为淡黄色晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于补骨脂。

用途

• 具有抗血管生成活性
• 抑制肿瘤
• 抑制肿瘤血管生成
• 抗骨质疏松的作用
• 用于含量测定/鉴定/药理实验等

反应信息

• 作为反应物：
  描述：

  甲基补骨脂黄酮A 在 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4'-O-甲基补骨脂查尔酮
  参考文献：
  名称：

  作为抗癌剂的新型巴伐奇宁类似物的合成和生物学评价

  摘要：

  已经合成了 28 种巴伐奇宁类似物的文库，包括脂肪族和芳香族醚、环氧化物、查耳酮、肟、氨基脲、肟醚和三唑衍生物，并评估了对四种不同人类癌细胞系的细胞毒性。与巴伐奇宁相比，许多类似物的生物评估研究显示出更好的细胞毒性特征。观察到 1,2,3-三唑类似物 ( 17i)对肺 (A549)、前列腺 (PC-3)、结肠 (HCT-116) 和乳腺的 IC 50值为7.72、16.08、7.13和 11.67 μM 的最佳结果(MCF-7) 癌细胞系。这种类似物对 HCT-116 和 A549 细胞系的细胞毒性比亲本分子提高了三倍和四倍（1）。对所有合成的类似物进行了结构活性关系 (SAR) 研究。此外，先导分子 ( 17i )的机理研究表明，它可抑制人结肠癌细胞 (HCT-116) 的集落形成和体外迁移。此外，它诱导形态学变化并介导 HCT-116 细胞的凋亡细胞死亡，其中线粒体膜电位 (MMP) 和

  DOI：

  10.1016/j.ejmech.2018.01.006
• 作为产物：
  描述：

  bavachinin 在 Chiralpak OZ-H column 作用下， 以 乙醇 为溶剂， 40.0 ℃ 、10.0 MPa 条件下， 生成 (R)-bavachinin 、 甲基补骨脂黄酮A
  参考文献：
  名称：

  Separation and peroxisome proliferator-activated receptor-γ agonist activity evaluation of synthetic racemic bavachinin enantiomers

  摘要：

  Bavachinin, isolated from Psoralea corylifolia seeds, has been reported to demonstrate peroxisome proliferator- activated receptor-gamma (PPAR-gamma) agonist activity. However, isolated bavachinin is actually a mixture of S and R configurations, with an enantiomeric excess value of approximately 24.3%. For further study on the structure-activity relationships of bavachinin, investigating the PPAR-gamma agonist activity of the two enantiomers is crucial. Considering the limited availability, racemic bavachinin was prepared in this study using chemical synthesis. The enantiomers of racemic bavachinin were then separated using supercritical fluid chromatography. This concise strategy yielded (S)- and (R)-bavachinin in optical purity as high as >= 97.5%. The PPAR-gamma agonist activity of the two enantiomers was evaluated using a time-resolved fluorescence resonance energy transfer-based competitive binding assay method; IC50 values of (S)-and (R)-bavachinin were 616.7 and 471.2 nM, respectively. The interaction between the compounds and PPAR-gamma was further explored using a molecular docking method. This study suggests that (S)-and (R)-bavachinin demonstrate similar PPAR-gamma agonist activities. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.029

文献信息

• Structural elucidation of<i>in vitro</i>metabolites of bavachinin in rat liver microsomes by LC-ESI-MSⁿand chemical synthesis
  作者：Fan Xie、Guoxin Du、Shunan Ma、Yiming Li、Rui Wang、Fujiang Guo

  DOI：10.3109/00498254.2015.1074763

  日期：2016.4.2

  Bavachinin isolated from Psoralea corylifolia has various activities, such as antimicrobial, antiallergic, antitumor and so on. Our previous study showed that natural bavachinin exhibits peroxisome proliferator-activated receptor gamma-agonist activity.In vitro studies on bavachinin metabolism were conducted using rat liver microsomes incubated at 37 degrees C for 60 min.Structures of eight metabolites of the incubation mixtures were cautiously characterized using electrospray tandem mass spectra and three synthetic compounds. The results indicated that eight metabolites of bavachinin were biotransformed mainly through oxidation.The metabolic pathways of bavachinin were elucidated in vitro. These results contribute to the understanding of bavachinin's in vivo metabolism.
• COMPOUNDS AND METHODS FOR TREATING ESTROGEN RECEPTOR-RELATED DISEASES
  申请人：Shenogen Pharma Group Ltd.

  公开号：EP2096916A2

  公开（公告）日：2009-09-09
• US8252835B2
  申请人：——

  公开号：US8252835B2

  公开（公告）日：2012-08-28
• [EN] COMPOUNDS AND METHODS FOR TREATING ESTROGEN RECEPTOR-RELATED DISEASES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR TRAITER DES MALADIES LIÉES À UN RÉCEPTEUR D'OESTROGÈNE
  申请人：SHENOGEN PHARMA GROUP LTD

  公开号：WO2008052005A2

  公开（公告）日：2008-05-02

  [EN] Provided herein in certain embodiments are compounds, pharmaceutical compositions and methods for modulating the functions of estrogen receptor alpha 36, for preventing and/or treating diseases related to estrogen receptor alpha 36, for preventing and/or treating respiratory diseases such as asthma, for inducing cell death and/or inhibiting cell proliferation and for preventing and/or treating diseases involving abnormal cell proliferation such as cancers.
  [FR] L'invention concerne, selon certains modes de réalisation, des composés, des compositions pharmaceutiques et des procédés pour moduler les fonctions d'un récepteur d'oestrogène alpha 36, pour empêcher et/ou traiter des maladies liées au récepteur d'oestrogène alpha 36, pour empêcher et/ou traiter des maladies respiratoires telles que l'asthme, pour induire une mort cellulaire et/ou empêcher une prolifération de cellules et pour empêcher et/ou traiter des maladies impliquant une prolifération anormale de cellules, telles que le cancer.
• Synthesis and biological evaluation of novel bavachinin analogs as anticancer agents
  作者：Nidhi Gupta、Arem Qayum、Arun Raina、Ravi Shankar、Sumeet Gairola、Shashank Singh、Payare L. Sangwan

  DOI：10.1016/j.ejmech.2018.01.006

  日期：2018.2

  A library of 28 analogs of bavachinin including aliphatic and aromatic ethers, epoxide, chalcone, oxime, semicarbazide, oxime ether and triazole derivatives have been synthesized and evaluated for cytotoxicity against four different human cancer cell lines. Bio-evaluation studies exhibited better cytotoxic profile for many analogs compare to bavachinin. Best results were observed for a 1,2,3-triazole

  已经合成了 28 种巴伐奇宁类似物的文库，包括脂肪族和芳香族醚、环氧化物、查耳酮、肟、氨基脲、肟醚和三唑衍生物，并评估了对四种不同人类癌细胞系的细胞毒性。与巴伐奇宁相比，许多类似物的生物评估研究显示出更好的细胞毒性特征。观察到 1,2,3-三唑类似物 ( 17i)对肺 (A549)、前列腺 (PC-3)、结肠 (HCT-116) 和乳腺的 IC 50值为7.72、16.08、7.13和 11.67 μM 的最佳结果(MCF-7) 癌细胞系。这种类似物对 HCT-116 和 A549 细胞系的细胞毒性比亲本分子提高了三倍和四倍（1）。对所有合成的类似物进行了结构活性关系 (SAR) 研究。此外，先导分子 ( 17i )的机理研究表明，它可抑制人结肠癌细胞 (HCT-116) 的集落形成和体外迁移。此外，它诱导形态学变化并介导 HCT-116 细胞的凋亡细胞死亡，其中线粒体膜电位 (MMP) 和