3-羟基月桂 酸 | 1883-13-2

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 3-羟基月桂 酸
• 中文别名: (±)-3-羟基月桂酸；3-羟基月桂酸
• 英文名称: 3-hydroxydodecanoic acid
• 英文别名: 3-hydroxylauric acid；(R,S)-3-hydroxy-dodecanoic acid；β-hydroxydodecanoic acid
• CAS: 1883-13-2
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: MUCMKTPAZLSKTL-UHFFFAOYSA-N

物化性质

• 熔点：
  70-70.5 °C
• 沸点：
  113-115 °C(Press: 3 Torr)
• 密度：
  0.987±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  3.110 (est)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2918199090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: DL-β-Hydroxylauric acid
Product name
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. : 1883-13-2
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 toxicity, Oral (Category 4), H302
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
Xn Harmful R22
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)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 3-Hydroxydodecanoic acid
Formula : C12H24O3
Molecular Weight : 216,32 g/mol
CAS-No. : 1883-13-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
DL-β-Hydroxylauric acid
CAS-No. 1883-13-2 Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
DL-β-Hydroxylauric acid
CAS-No. 1883-13-2 Xn, R22 <= 100 %
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
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.
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: 2 - 8 °C
Specific end use(s)
Apart 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
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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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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) 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: 3,462
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
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: - 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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，3-羟基十二酸是一种中链脂肪酸，与脂肪酸代谢性疾病相关。靶点为：

• 人类内源性代谢物

注：此处的“人类内源性代谢物”是基于表格内容的理解进行的润色。原文中的表格包含了一些空白行和多余标签，已进行了简化处理。

反应信息

• 作为反应物：
  描述：

  3-羟基月桂 酸 生成 2-甲基癸醇
  参考文献：
  名称：

  Thaler; Staehlin, Biochemische Zeitschrift, 1949, vol. 320, p. 86

  摘要：

  DOI：
• 作为产物：
  描述：

  癸醛 在 tetrabutylammonium borohydride 、 tin(ll) chloride 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 26.0h， 生成 3-羟基月桂 酸
  参考文献：
  名称：

  连续的荧光Sirtuin 2脱酰基酶测定：底物筛选和抑制剂评估

  摘要：

  Sirtuins是赖氨酸酰化的重要调节剂，其与细胞代谢和转录控制有关。这使得sirtuin类酶成为开发具有药物潜力的小分子探针的有趣靶标。为了获得有关瑟土因抑制剂的详细分析和动力学见解，重要的是要获得有效的测定方法。在这项工作中，我们报告了易于合成的荧光底物，能够以连续测定形式对SIRT2抑制剂进行酶经济评价，以及对SIRT2作为长链脱酰基酶的特性进行评价。因此，在体外建立了SIRT2的新酶活性，需要进一步研究，并且针对含有ε- N的底物分析了两种已知的抑制剂，苏拉明和SirReal2。-不同长度的酰基赖氨酸修饰。

  DOI：

  10.1021/acs.jmedchem.5b01532

文献信息

• Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
  作者：Andrew Giltrap、Katie Cergol、Angel Pang、Warwick Britton、Richard Payne

  DOI：10.3390/md11072382

  日期：——

  The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative

  报告了海洋衍生的脂肽天然产物 flutamide B 和脱氧 fellutamides B、C 和 D 的全合成。这些化合物是通过使用 Weinreb 酰胺衍生树脂的新型固相合成策略获得的。作为合成的一部分，利用布朗烯丙基化反应和氧化裂解-氧化序列作为关键步骤开发了一种新的 (3R)-羟基月桂酸的对映选择性路线。这些天然产物和天然产物类似物的活性也在体外针对结核分枝杆菌进行了评估。
• The Synthesis of Medium-Chain-Length β-Hydroxy Esters via the Reformatsky Reaction
  作者：John Sorensen、Miloslav Sailer、Krystyn Dubicki

  DOI：10.1055/s-0034-1379479

  日期：——

  esters in good yield via the Reformatsky reaction is described. This work will be used as the basis for further investigation of hydroxyalkanoate polymers as potential feedstock for biofuel production. The synthesis of medium-chain-length β-hydroxy esters in good yield via the Reformatsky reaction is described. This work will be used as the basis for further investigation of hydroxyalkanoate polymers

  摘要 描述了通过Reformatsky反应以高收率合成中链长度的β-羟基酯。这项工作将用作进一步研究羟基链烷酸酯聚合物作为生产生物燃料的潜在原料的基础。 描述了通过Reformatsky反应以高收率合成中链长度的β-羟基酯。这项工作将用作进一步研究羟基链烷酸酯聚合物作为生产生物燃料的潜在原料的基础。
• Methods of making intermediates from polyhydroxyalkanoates
  申请人：——

  公开号：US20030144551A1

  公开（公告）日：2003-07-31

  Methods of forming intermediates from PHAs are disclosed.

  从PHA中形成中间体的方法已被披露。
• ANTIMICROBIAL AGENT
  申请人：Kanatani Shuji

  公开号：US20150005378A1

  公开（公告）日：2015-01-01

  [Problem] To provide a novel antimicrobial agent that has excellent antimicrobial activity and which is prepared from an ester composed of propanediol and a β-hydroxycarboxylic acid. [Solution] An antimicrobial agent which is prepared from a propanediol mono-β-hydroxycarboxylic acid ester expressed by the following formula (1) or formula (2) (wherein R 1 and R 2 are both branched or unbranched, and saturated or unsaturated alkyl groups having 5 to 9 carbon atoms).

  提供一种新型抗菌剂，具有优异的抗菌活性，由丙二醇和β-羟基羧酸组成的酯制备而成。从以下公式（1）或公式（2）表示的丙二醇单β-羟基羧酸酯制备的抗菌剂（其中R1和R2均为分支或非分支，饱和或不饱和的烷基，具有5至9个碳原子）。
• AMIDE COMPOUND OR SALT THEREOF, AND BIOFILM INHIBITOR, BIOFILM REMOVER AND DISINFECTANT CONTAINING THE SAME
  申请人：Suga Hiroaki

  公开号：US20090068120A1

  公开（公告）日：2009-03-12

  The present invention provides a new amide compound and salt thereof that is capable of inhibiting biofilm formation or removing deposited biofilms. The present invention also provides a biofilm formation inhibitor or a biofilm remover containing the amide compound or salt thereof as an active ingredient. An amide compound or salt thereof according to the present invention is denoted by General Formula (1): wherein R 1 is a hydrogen atom or a hydroxyl group, R 2 is a C 5-12 alkyl group, and Q is a substituent denoted by Formula (Q1) or (Q2), wherein n and m are 0 or 1.

  本发明提供了一种新的酰胺化合物及其盐，能够抑制生物膜的形成或去除已沉积的生物膜。本发明还提供了一种含有该酰胺化合物或其盐作为活性成分的生物膜形成抑制剂或生物膜去除剂。根据本发明的酰胺化合物或其盐由通式（1）表示：其中R1是氢原子或羟基，R2是C5-12烷基基团，Q是由通式（Q1）或（Q2）表示的取代基，其中n和m为0或1。