异海松酸 | 5835-26-7

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 异海松酸
• 英文名称: isopimaric acid
• 英文别名: (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• CAS: 5835-26-7
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: MXYATHGRPJZBNA-KRFUXDQASA-N

物化性质

• 熔点：
  160°
• 比旋光度：
  D16 -3.6° (10.4% soln in 1:1 alcohol:chloroform)
• 沸点：
  383.47°C (rough estimate)
• 密度：
  1.0434 (rough estimate)
• 溶解度：
  二甲基亚砜：~26 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 储存条件：
  -20℃，密封保存，置于干燥处。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Isopimaric Acid
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. : 5835-26-7

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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
For the full text of the H-Statements mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
Very toxic to aquatic life.
Precautionary statement(s)
Avoid release to the environment.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C20H30O2
Molecular Weight : 302,45 g/mol
CAS-No. : 5835-26-7
No components need to be disclosed according to the applicable regulations.
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
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
Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate
personnel to safe areas.
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: powder
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) 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- no data available
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
Toxicity to fish LC50 - Pimephales promelas (fathead minnow) - 0,87 mg/l - 96 h
Persistence and degradability
Bioaccumulative potential
Bioaccumulation Oncorhynchus mykiss (rainbow trout) - 14 d
- 2,7 µg/l
Bioconcentration factor (BCF): 34
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.
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. (Isopimaric Acid)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Isopimaric Acid)
IATA: Environmentally hazardous substance, solid, n.o.s. (Isopimaric Acid)
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
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，isopimaric acid 是一种有效的大型钙激活钾通道（大电导钙激活钾通道，简称 BK 通道）的开放剂。

反应信息

• 作为反应物：
  描述：

  异海松酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到(1R,4aR,4bS,7S,10aR)-1,4a,7-trimethyl-7-ethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid
  参考文献：
  名称：

  高级萜类化合物的合成转化。XXXIII.* 15,16-二氢异海松酸和二氢异海松酸甲酯的制备及其转化

  摘要：

  提出了制备15,16-二氢异海松酸及其甲酯的方法。二氢异海松酸甲酯在 3-氯过苯甲酸的作用下发生氧化，形成 7,8-环氧衍生物和 7α-羟基二氢山达海松酸。除了 7-氧代四氢异海松酸酯外，后者还通过叔丁基过氧化氢在 MoCl5 存在下的作用形成。二氢异海松酸或酯在二恶烷中被二氧化硒氧化得到相应的 14α-羟基衍生物。氯铬酸吡啶将 14α-羟基二氢异海松酸转化为 7α-羟基-8,14-环氧异海松酸、7-氧-8,14-环氧异海松酸、7-氧-14-羟基异海松酸和 7α-羟基山达拉海松酸甲酯的混合物。在 NaOAc 存在下，在 MeOH 中通过盐酸羟胺对 7-氧代四氢异海松酸甲酯进行肟化，得到相应的 (Z)-和 (E)-肟的混合物。通过亚硫酰氯的作用，四氢异海松酸甲酯的 7-(E)-肟的贝克曼重排产生了十四氢二苯并[b,d]氮杂。

  DOI：

  10.1007/s10600-014-0823-1
• 作为产物：
  描述：

  isopimaric acid chloride 、 聚甘氨酸 在 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以31%的产率得到
  参考文献：
  名称：

  高级萜类化合物的合成转化。39.*异海松酸衍生物的合成及镇痛活性

  摘要：

  制备了异海松酸羧酸的新衍生物。在内脏痛和热痛模型中研究了它们的镇痛活性。异海松酸酰胺与氨基乙醇和 (2 R )-（羟甲基）吡咯烷组在乙酸诱导的扭体（5 和 25 mg/kg 剂量）和热板试验（25 mg/kg 剂量）中表现出统计学上显着的镇痛活性。与双氯芬酸钠（10 mg/kg 剂量）相当。新药剂的特点是体内毒性低（LD 50 > 1250 mg/kg）。对最活跃的化合物与跨膜 G 蛋白结合大麻素受体 CB 2的可能相互作用进行了分子建模。

  DOI：

  10.1007/s10600-021-03391-1

文献信息

• [EN] ANTIBIOFILM FORMULATIONS<br/>[FR] FORMULATIONS D'ANTIBIOFILM
  申请人：UNIV NORTHERN ARIZONA

  公开号：WO2018222924A1

  公开（公告）日：2018-12-06

  Methods and compositions related to molecules and formulations comprising antibiofilm materials are provide, including new formulations of Deep Eutectic Solvents (DES) that are chemically related to choline geranate. Specifically, geranic acid (a component of choline geranate DES) is a molecule from the isoprenoid/terpene family of compounds. Other members of this family as DES components include isoprenoid acids and chemical derivatives thereof.

  提供与分子和配方相关的方法和组合物，其中包括含有抗生物膜材料的新配方，其中这些配方包括与胆碱油酸盐化物相关的新型深共熔溶剂（DES）。具体来说，油酸（胆碱油酸盐化物DES的一种成分）是异戊二烯/萜类化合物家族中的一种分子。该家族的其他成员作为DES组分包括异戊二烯酸及其化学衍生物。
• HEAT-RESISTANT ALIPHATIC-CHAIN SATURATED HYDROCARBON HAVING ION PAIRS AT BOTH ENDS, AND COMPOSITION USING SAME
  申请人：Kaneka Corporation

  公开号：US20180029992A1

  公开（公告）日：2018-02-01

  An aliphatic-chain saturated hydrocarbon including an aliphatic hydrocarbon chain which is saturated and has an ion pair at each end of the aliphatic hydrocarbon chain.

  一种包括饱和脂肪烃链的脂肪链饱和烃，该脂肪烃链是饱和的，并且在脂肪烃链的每一端具有一个离子对。
• Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes
  作者：M. A. Gromova、Yu. V. Kharitonov、T. V. Rybalova、E. E. Shul’ts

  DOI：10.1007/s10600-018-2327-x

  日期：2018.3

  The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its condensation with α-amino acids. The structures of the synthesized compounds were confirmed by IR, UV, and NMR spectral data and an XSA.

  研究了将异海松酸甲酯氧化为15-氧代-15,16-二氢异海松酸的条件。后者被用于一步法合成13-(噁唑-5-基)-15,16-双降异海松酸，其中包括形成16-氧代醛异海松酸及其与α-氨基酸的缩合。通过IR、UV、NMR光谱数据和XSA分析，确认了合成化合物的结构。
• Synthetic Transformations of Higher Terpenoids. XXXIV.* Preparation of Carboxyl Derivatives of Isopimaric Acid
  作者：M. A. Timoshenko、A. B. Ayusheev、Yu. V. Kharitonov、M. M. Shakirov、E. E. Shul’ts

  DOI：10.1007/s10600-014-1050-5

  日期：2014.10

  New isopimaric acid derivatives containing amines and methyl esters of α-, β-, and ω-amino acids were prepared. Conditions were found for cyclic isomerisation of isopimaric acid propargylamide into 2-(dodecahydrophenanthren-1-yl)-5-methyloxazole or 2-(dodecahydrophenanthren-1-yl)-5-methylene-4,5-dihydrooxazole. The latter was selectively modified by adding the methyl ester of (2-methylamino)butanoic

  制备了含有胺和α-、β-和ω-氨基酸甲酯的新异海松酸衍生物。发现异海松酸炔丙酰胺循环异构化成2-(十二氢菲-1-基)-5-甲基恶唑或2-(十二氢菲-1-基)-5-亚甲基-4,5-二氢恶唑的条件。后者通过在恶唑 C-5 位添加（2-甲基氨基）丁酸甲酯进行选择性修饰。
• [EN] METATHESIS CATALYSTS AND METHODS THEREOF<br/>[FR] CATALYSEURS DE MÉTATHÈSE ET PROCÉDÉS ASSOCIÉS
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2016073750A1

  公开（公告）日：2016-05-12

  The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and/or stereoselectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and Z-selectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and E-selectivity. In some embodiments, provided technologies are particularly useful for preparing alkenyl fluorides. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-a. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-b.

  本申请提供了化合物和用于交换反应的方法，其中包括用于制备烯烃卤化物的具有区域选择性和/或立体选择性的方法。在某些实施例中，本公开提供了用于具有区域选择性和Z-选择性的烯烃卤化物的制备方法。在某些实施例中，本公开提供了用于具有区域选择性和E-选择性的烯烃卤化物的制备方法。在某些实施例中，提供的技术特别适用于制备烯烃氟化物。在某些实施例中，用于交换反应的提供的化合物具有II-a式的结构。在某些实施例中，用于交换反应的提供的化合物具有II-b式的结构。