16-溴-1-十六烷醇 | 59101-28-9

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 16-溴-1-十六烷醇
• 中文别名: 16-溴十六-1-醇；16-溴十六醇
• 英文名称: 16-bromohexadecan-1-ol
• 英文别名: 16-bromo-1-hexadecanol；16-bromohexadecanol；1-bromohexadecan-16-ol
• CAS: 59101-28-9
• 化学式: C₁₆H₃₃BrO
• mdl: MFCD01076224
• 分子量: 321.341
• InChiKey: GOSQZSJMSMTIFI-UHFFFAOYSA-N

物化性质

• 熔点：
  45-52°C
• 沸点：
  383.7±15.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)
• 闪点：
  >110℃

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36/37/39
• WGK Germany：
  3
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 16-Bromo-1-hexadecanol
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. : 59101-28-9
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 1-Bromohexadecane-16-ol
Formula : C16H33BrO
Molecular Weight : 321,34 g/mol
CAS-No. : 59101-28-9
No components need to be disclosed according to the applicable regulations.

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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, Hydrogen bromide gas
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. 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 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.
Handle under nitrogen, protect from moisture. Store under nitrogen. Moisture sensitive.
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
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 Melting point/range: 45 - 52 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point > 110 °C
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
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

反应信息

• 作为反应物：
  描述：

  16-溴-1-十六烷醇 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以98%的产率得到16-碘十六烷-1-醇
  参考文献：
  名称：

  Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

  摘要：

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.002
• 作为产物：
  描述：

  氧杂环十七烷-2-酮 在 二异丁基氢化铝 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 16-溴-1-十六烷醇
  参考文献：
  名称：

  钯催化的高度取代的 α,β-不饱和羰基化合物的长程解共轭异构化

  摘要：

  描述了通过原位生成的氢化钯催化剂对各种 α,β-不饱和酰胺、酯和酮进行长程解共轭异构化。这种氧化还原经济过程由加氢金属化事件触发，并由伯醇或仲醇再官能化为醛或酮的热力学驱动。二、三和四取代的碳-碳双键反应效率相似；该系统对多种官能团具有耐受性，并且烯烃迁移可以持续超过 30 个碳原子。再官能化的产物通常以良好到极好的产率分离。机理研究支持由重复迁移插入和 β-H 消除组成的链行走过程。异构化反应的双向性是通过同位素标记实验建立的，该实验使用具有与两个末端功能分离的双键的底物。还发现氢化钯直接参与形成产物的互变异构步骤。使用异构的三取代 α,β-不饱和酯证明了原位生成的 [Pd-H] 的两亲性特征。最后，在一小组α-取代的α，β-不饱和酮的异构化中获得的高水平对映选择性预示着这种非常规异构化的对映选择性版本的成功开发。还发现氢化钯直接参与形成产物的互变异构步骤。使用异构的三取代 α,β-不饱和酯证明了原位生成的

  DOI：

  10.1021/jacs.6b06390

文献信息

• Polymerization of macrocyclic phospholipid- and surfactant-based vesicles
  作者：Steven L. Regen、N. K. P. Samuel、Jitender M. Khurana

  DOI：10.1021/ja00306a039

  日期：1985.10

  II-mercaptoundecanoyl)-sn-glycero-3-phosphocholine can be polymerized as well as depolymerized in vesicle form, via a thiol-disulfide redox cycle.2 Two intriguing questions regarding the polymerization process are the focus of the present work: Are nonsymmetrical lipids necessary for interlipid coupling, Le., vesicle polymerization? Are the resulting polymers formed under thermodynamic or kinetic control? Phosphatidylcholines

  我们最近表明，1,2-双（II-巯基十一烷酰基）-sn-甘油-3-磷酸胆碱可以通过硫醇-二硫化物氧化还原循环以囊泡形式聚合和解聚。 2 关于聚合过程的两个有趣问题是当前工作的重点：非对称脂质对于脂质间偶联（即囊泡聚合）是必需的吗？所得聚合物是在热力学还是动力学控制下形成的？已知处于双层状态的磷脂酰胆碱更喜欢甘油骨架大致垂直于膜平面的构象，其中两条脂肪酸链不等地延伸。）基于这一事实，我们之前曾建议，在每个 a 和 3 链中位于相同碳原子处的硫醇基团将被隔离，并且脂质间氧化偶联将占主导地位。2,4 然而，该过程是否会在热力学上受到青睐并未得到解决. 我们现在表明大环二硫化物类似物 1，以及对称的
• Cyclohexenonic Long-Chain Fatty Alcohols as Neuronal Growth Stimulators
  作者：Bang Luu、José-Luis De Aguilar、Céline Girlanda-Junges

  DOI：10.3390/51201439

  日期：——

  Neurotrophic factors play an important role in the development and maintenance of neurons, thus providing a suitable therapeutic approach for the treatment of neurodegenerative diseases. However, their clinical use has revealed problematic because of a number of technical and biological disadvantages. Among the different strategies proposed to overcome such difficulties, the search for non-peptide substances with neurotrophic potential is giving promising results. Here we will expose major findings in this field, drawing special attention to cyclohexenonic long-chain fatty alcohols, a novel family of compounds that promote neuronal survival and neurite outgrowth.

  神经营养因子在神经元的发育和维持中起着重要作用，因此为治疗神经退行性疾病提供了合适的疗法。然而，由于存在一系列技术和生物学上的缺点，它们在临床应用中遇到了问题。在提出的不同克服这些困难的策略中，寻找具有神经营养潜力的非肽类物质正取得令人鼓舞的成果。本文将展示该领域的主要发现，特别关注环己烯型长链脂肪醇，这是一个促进神经元存活和神经突延伸的新型化合物家族。
• ACTIVE-ENERGY-RAY-POLYMERIZABLE INITIATOR, ACTIVE-ENERGY-RAY-POLYMERIZABLE COMPOSITION, ACTIVE-ENERGY-RAY-POLYMERIZABLE INK, INK STORAGE CONTAINER, IMAGE FORMING METHOD, AND IMAGE FORMING APPARATUS
  申请人：HARADA Shigeyuki

  公开号：US20200270469A1

  公开（公告）日：2020-08-27

  An active-energy-ray-polymerizable initiator having a structure represented by the following general formula (1) is provided. In general formula (1), L 1 represents —C(═O)—O— (binding to L 2 side) or —O—, L 2 represents —O(CH 2 ) p -(binding to L 1 side), —(OC 2 H 4 ) n -(binding to L 1 side), or —(OC 3 H 6 ) m -(binding to L 1 side), where p represents an integer of 2 to 16, n represents an integer of 2 to 12, and m represents 2 or 3, L 3 represents a direct binding or —NH—, L 4 represents —OC 2 H 4 -(binding to L 3 side) or —(OC 2 H 4 ) 2 -(binding to L 3 side), and R represents —H or —CH 3 .

  提供具有以下一般式（1）所代表的结构的活性能量射线可聚合引发剂。 在一般式（1）中，L1代表—C(═O)—O—（与L2侧结合）或—O—，L2代表—O(CH2)p-(与L1侧结合)，—(OC2H4)n-(与L1侧结合)，或—(OC3H6)m-(与L1侧结合)，其中p表示2到16的整数，n表示2到12的整数，m表示2或3，L3代表直接结合或—NH—，L4代表—OC2H4-(与L3侧结合)或—(OC2H4)2-(与L3侧结合)，R代表—H或—CH3。
• Design, synthesis and biological evaluation of novel pyrazolone derivatives as selective butyrylcholinesterase inhibitors with antioxidant activity against Alzheimer's disease
  作者：Zhipeng Zhang、Maojun Cheng、Jie Guo、Yang Wan、Rikang Wang、Yuanying Fang、Yi Jin、Sai-Sai Xie、Jing Liu

  DOI：10.1016/j.molstruc.2021.132319

  日期：2022.4

  activities, antioxidant activities and blood-brain barrier (BBB) permeabilities. Besides, the compounds 5g, 5h, 5i and 5o with submicromolar IC50 values as well as good BuChE selectivity were chosen to assess their cytotoxicity in PC12 cells. Among them, compound 5i was the most selective BuChE inhibitor (SI: >200) and showed the good abilities to penetrate BBB, scavenge free radicals (1.04 trolox equivalent)

  丁酰胆碱酯酶 (BuChE) 一直是治疗阿尔茨海默病 (AD) 的有效靶点，但市场上仍缺乏选择性 BuChE 抑制剂。在这项研究中，发现吡唑啉酮结构是一种很有前途的靶向 BuChE 的药效团。因此，设计、合成了一系列基于吡唑啉酮的化合物5a-p，并在体外评估了 BuChE 抑制活性、抗氧化活性和血脑屏障 (BBB) 渗透性。此外，选择具有亚微摩尔IC 50值以及良好的BuChE选择性的化合物5g、5h、5i和5o来评估它们在PC12细胞中的细胞毒性。其中，化合物5i是最具选择性的 BuChE 抑制剂（SI：>200），并显示出良好的穿透 BBB、清除自由基的能力（1.04 trolox 当量）。基于上述结果，化合物5i被选择用于分子对接研究以解释 BuChE 的选择性，并被认为是一种有前途的先导化合物，可用于进一步研究 AD 的治疗。
• Macrolide formation by free radical cyclization
  作者：Ned A. Porter、Vincent H. T. Chang

  DOI：10.1021/ja00250a036

  日期：1987.8

  Etude de la synthese de macrocycles ayant au moins 11 chainons par addition intramoleculaire radicalaire d'acrylates d'ω-iodoalkyle ou de fumarates d'ethyle et ω-iodoalkyle. Cinetique

  大环合成练习曲 ayant au moins 11 链子par加成分子内自由基 d'丙烯酸酯 d'ω-碘代烷基 ou de fumarates d'乙基和 ω-碘代烷基。电影