D-赤藓-鞘氨醇磷酸胆碱 | 1670-26-4

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: D-赤藓-鞘氨醇磷酸胆碱
• 英文名称: sphingosylphosphorylcholine
• 英文别名: SPC；lysosphingomyelin；lysoSM (d18:1)；[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 1670-26-4
• 化学式: C₂₃H₄₉N₂O₅P
• 分子量: 464.626
• InChiKey: JLVSPVFPBBFMBE-HXSWCURESA-N

物化性质

• 熔点：
  90-102°C
• 溶解度：
  在氯仿/甲醇(2:1)中的溶解度:10mg/ml,无色至淡黄色

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 储存条件：
  -20℃

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Sphingosylphosphorylcholine
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. : 1670-26-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

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

---

SECTION 3: Composition/information on ingredients
Substances
Synonyms : 2-[[[(2-Amino-3-hydroxy-4-octadecenyl)oxy]hydroxy-phosphinyl]oxy]-
N,N,N-trimethylethanaminiuminner salt
Lysosphingomyelin
Formula : C23H49N2O5P
Molecular Weight : 464,62 g/mol
CAS-No. : 1670-26-4
No components need to be disclosed according to the applicable regulations.

---

SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
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

---

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, nitrogen oxides (NOx), Oxides of phosphorus
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

---

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
Keep in a dry place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
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.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: light yellow
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

---

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

---

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.

---

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

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

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

---

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
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  D-赤藓-鞘氨醇磷酸胆碱 在 4-甲基哌啶 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.84h， 生成
  参考文献：
  名称：

  脂肪酰基辅酶A连接酶的表达驱动无细胞转录翻译系统中膜结合囊泡的一锅法从头合成

  摘要：

  尽管脂质膜在细胞组织中具有核心重要性，但从最少的化学和生物元素重新构建它们的形成是具有挑战性的。在这里，我们描述了形成膜的非经典磷脂的化学酶途径，其中半胱氨酸修饰的溶血脂与脂肪酰基-CoA 连接酶酶促产生的脂肪酰基-CoA 硫酯发生自发偶联。由于反应的高效率，我们能够优化无细胞转录翻译 (TX-TL) 系统中的磷脂形成。将编码脂肪酰基辅酶A连接酶的DNA与合适的脂质前体相结合，可以实现一锅从头膜结合囊泡的合成。通过使用半胱氨酸修饰的溶血鞘磷脂作为前体，也可以合成非常规的鞘脂。当鞘磷脂相互作用蛋白lysenin与酰基辅酶A连接酶共表达时，原位组装的膜自发地被蛋白质修饰。我们以一锅方式将基因表达与膜脂合成结合的策略可以促进蛋白脂质体的产生，并使我们更接近使用重组合成生物学平台自下而上生成合成细胞。

  DOI：

  10.1021/jacs.1c05394
• 作为产物：
  描述：

  (2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol 在 咪唑 、 1,3-丙二硫醇 、 4-二甲氨基吡啶 、 四甲基乙二胺 、 四丁基氟化铵 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 136.0h， 生成 D-赤藓-鞘氨醇磷酸胆碱
  参考文献：
  名称：

  鞘磷脂的改进，多功能和易于扩展的合成：在稳定同位素标记中的应用

  摘要：

  为了提供方便地标记的质谱标准物，以2-叠氮基-3- O-苯甲酰鞘氨醇为关键，通过一种新的简便，灵活，耐用，可扩展且高产的合成方案制备了一组氘代鞘磷脂中间。与以前发布的程序不同，这项工作强调了在麻烦但关键的磷酸化步骤中选择叠氮基官能团作为反应性伯胺的掩蔽基团的好处。

  DOI：

  10.1055/s-0039-1690863
• 作为试剂：
  描述：

  对甲氧基苯乙酮 在 1,3-二硝基苯 过氧碳酸钠 、 potassium tert-butylate 、 D-赤藓-鞘氨醇磷酸胆碱 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 以58%的产率得到大茴香酸
  参考文献：
  名称：

  过碳酸钠或过硼酸钠作为末端氧化剂的硝基芳烃催化氧化

  摘要：

  报道了一种由甲基芳基酮制备芳族羧酸的新型催化氧化方法。该方法是卤仿反应的替代方法。它是良性的，可提供所需的产品，而不会产生任何有害的副产品。催化循环基于使用缺电子的硝基芳烃作为催化剂，同时使用两种廉价的绿色氧化剂过碳酸钠或过硼酸钠。当模型底物（苯乙酮）被氧化时，该方法收率良好（87％），并且显示出极好的选择性。通过这种方法制备了一系列工业上有意义的苯甲酸。

  DOI：

  10.1016/j.tetlet.2004.09.156

文献信息

• The critical micelle concentrations of lysophosphatidic acid and sphingosylphosphorylcholine
  作者：Zaiguo Li、Evan Mintzer、Robert Bittman

  DOI：10.1016/j.chemphyslip.2004.03.001

  日期：2004.7

  The critical micelle concentrations (CMC) of lysophosphatidic acid (LPA) and sphingosylphosphorylcholine (SPC) were measured by isothermal titration calorimetry. The CMC of LPA decreases with salt concentration and acyl chain length. In water at 25 degrees C, the CMC values of 1-acyl-2-lyso-sn-glycero-3-phosphatidic acid are 1.850, 0.540, 0.082, and 0.346 mM, respectively, when the acyl group is myristoyl

  通过等温滴定量热法测定了溶血磷脂酸（LPA）和鞘氨醇磷酸胆碱（SPC）的临界胶束浓度（CMC）。LPA的CMC随着盐浓度和酰基链长度的增加而降低。在25摄氏度的水中，当酰基为肉豆蔻酰基，棕榈酰基，硬脂酰基时，1-酰基-2-溶-sn-甘油-3-磷脂酸的CMC值分别为1.850、0.540、0.082和0.346 mM。和油酰基。SPC在25 mC，pH 7.4的10 mM磷酸钠缓冲液中的CMC为0.158 mM，并且不随盐浓度的增加而变化。
• Biomimetic Generation and Remodeling of Phospholipid Membranes by Dynamic Imine Chemistry
  作者：Andrés Seoane、Roberto J. Brea、Alberto Fuertes、Kira A. Podolsky、Neal K. Devaraj

  DOI：10.1021/jacs.8b04557

  日期：2018.7.11

  reaction of the natural amine-containing lysosphingomyelin with a series of long-chain aldehydes to form imines. This transformation results in the formation of phospholipid liposomes that are in dynamic equilibrium with the aldehyde-amine form. The reversibility of the imine linkage is exploited in the synthesis of vesicles that are capable of responding to external stimuli such as temperature or the

  仿生脂质体在多个领域有广泛的应用，从药物化学到合成生物学。由于它们的生物相容性和生物学相关性，人们对合成磷脂囊泡的形成和以受控方式调整其性质的方法的开发特别感兴趣。然而，虽然真正的生物膜能够通过酶促重塑其组成来响应环境刺激，但合成脂质体一旦形成通常是静态的。在此，我们报告了天然含胺溶血鞘磷脂与一系列长链醛形成亚胺的化学选择性反应。这种转化导致形成与醛-胺形式动态平衡的磷脂脂质体。
• [EN] SPHINGOMYELIN, INTERMEDIATES THEREOF AND METHODS FOR PREPARATION OF SAME<br/>[FR] SPHINGOMYELINE, SES INTERMEDIAIRES, ET SES PROCEDES DE PREPARATION
  申请人：BIOLAB LTD

  公开号：WO2005068480A1

  公开（公告）日：2005-07-28

  The invention concerns novel oxazaphospholanes, cyclic and acyclic, and to their use in the synthesis of sphingomyelin and sphingomyelin analogous as well as to synthetic sphingomyelins obtained therefrom. One group of oxazaphospholane according to the invention has the general formula (1) disclosed herein. Specifically, the invention provides the 2S, 3R stereoisomers of the disclosed oxazaphospholanes and sphingomyelins and synthetic methods for their preparation.

  本发明涉及新型的氧氮杂磷杂环和环状氧氮杂磷杂环，以及它们在合成鞘磷脂和类似鞘磷脂中的应用，以及由此获得的合成鞘磷脂。根据本发明的一组氧氮杂磷杂环具有此处公开的通用公式(1)。具体而言，本发明提供了所述氧氮杂磷杂环和鞘磷脂的2S, 3R立体异构体及其制备方法。
• Red-Emitting Rhodamine Dyes for Fluorescence Microscopy and Nanoscopy
  作者：Kirill Kolmakov、Vladimir N. Belov、Jakob Bierwagen、Christian Ringemann、Veronika Müller、Christian Eggeling、Stefan W. Hell

  DOI：10.1002/chem.200902309

  日期：2010.1.4

  lipophilic and hydrophilic derivatives starting from the same chromophore‐containing scaffold are described. Introduction of two sulfo groups provides high solubility in water and a considerable rise in fluorescence quantum yield. The attachment of amino or thiol reactive groups allows the dyes to be used as fluorescent markers in biology. Dyes deuterated at certain positions have narrow and symmetrical molecular

  红色发出的荧光标记物在生物显微镜中非常有价值，因为它们可将细胞的自发荧光降至最低，并增加多色实验的灵活性。已开发出可在630 nm激光激发并在660 nm左右发射的新型若丹明染料。新的若丹明具有很高的光稳定性，并具有高达80％的高荧光量子产率，3.4 ns的长激发态寿命以及相对较低的系统间交叉速率。它们在常规和亚衍射分辨率显微镜（例如STED（受激发射损耗）和GSDIM（具有单个分子返回的基态损耗））以及基于单分子的实验（例如荧光相关光谱法（ FCS）。描述了从相同的含发色团的支架开始的亲脂性和亲水性衍生物的合成。两个磺基的引入提供了在水中的高溶解度和荧光量子产率的显着提高。氨基或硫醇反应性基团的附着使染料可用作生物学中的荧光标记。在某些位置氘化的染料具有狭窄且对称的分子量分布模式，被提议作为MS或LC-MS中的新标签，用于鉴定和定量复杂混合物中的各种物质类别（例如，胺和硫醇）。高分辨率G
• Syntheses of Sphingomyelins and Ceramides Bearing a Docosahexaenoyl or Arachidonoyl Group
  作者：Eiji MORIGAKI、Miyako NAGAO、Yoshie MIURA、Kyoya TAKAHATA、Mikiro TADA、Shuhei NAKAJIMA、Naomichi BABA、Sakayu SHIMIZU

  DOI：10.1271/bbb.62.2070

  日期：1998.1

  Sphingomyelins and ceramides bearing a docosahexaenoyl or arachidonoyl group were synthesized from sphingosylphosphorylcholine and sphingosine, respectively, by dicyclohexylcarbodiimide-mediated acylation.

  通过二环己基碳二亚胺介导的酰化反应，分别从鞘磷脂酰胆碱和鞘氨醇合成了具有二十碳六烯酰或花生四烯酰基团的鞘脂酰胺和神经酰胺。