2-氨基十八烷-1,3-二醇 | 13552-09-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氨基十八烷-1,3-二醇
• 英文名称: 2-aminooctadecan-1,3-diol
• 英文别名: dihydrosphingosine；Dihydro-sphingosin；2-amino-1,3-octadecanediol；sphinganine；(D,L)-2-amino-1,3-octadecanediol；D,L-threo-dihydro-sphingosine；2-Aminooctadecane-1,3-diol
• CAS: 13552-09-5
• 化学式: C₁₈H₃₉NO₂
• 分子量: 301.513
• InChiKey: OTKJDMGTUTTYMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2922199090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : DL-Dihydrosphingosine
CAS-No. : 13552-09-5
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 : 1,3-Dihydroxy-2-aminooctadecane
DL-1,3-Dihydroxy-2-aminooctadecane
Formula : C18H39NO2
Molecular Weight : 301,51 g/mol

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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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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, nitrogen oxides (NOx)
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 vapors, mist or gas.
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.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
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 uses
no data available

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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).

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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) Evaporation 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) Autoignition 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
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong acids, Strong bases
Hazardous decomposition products
Other decomposition products - no data available

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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 sensitization
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
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
no data available
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.
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

DL-1,3-二羟基-2-氨基十八烷是一种生物化学试剂，可用作生物材料或有机化合物，广泛应用于生命科学领域的相关研究。

反应信息

• 作为反应物：
  描述：

  2-氨基十八烷-1,3-二醇 在 吡啶 、 氢氧化钾 作用下， 生成 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadecyl)-benzamide
  参考文献：
  名称：

  STUDIES IN THE SPHINGOLIPIDS SERIES. I. SYNTHESIS OF RACEMIC 2-AMINO-1,3-DIHYDROXYOCTADECANE

  摘要：

  DOI：

  10.1021/jo01129a011
• 作为产物：
  描述：

  十六醛 在 palladium on activated charcoal 、 La-Li-6,6'-bis(((triethyl)silyl)ethenyl)-(R)-BINOL 氢气 作用下， 以 乙醇 为溶剂， 反应 163.0h， 生成 2-氨基十八烷-1,3-二醇
  参考文献：
  名称：

  Efficient Diastereoselective and Enantioselective Nitroaldol Reactions from Prochiral Starting Materials: Utilization of La-Li-6,6'-Disubstituted BINOL Complexes as Asymmetric Catalysts

  摘要：

  DOI：

  10.1021/jo00128a005

文献信息

• [EN] SPHINGOSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA SPHINGOSINE KINASE
  申请人：LYNCH KEVIN

  公开号：WO2016054261A1

  公开（公告）日：2016-04-07

  Sphingosine kinases are enzymes that catalyze the biosynthesis of sphingosine-1-phosphate. The invention provides compounds that are effective for inhibition of sphingosine kinase type 1, sphingosine kinase type 2, or both. Certain compounds are selective for sphingosine kinase type 2 relative to sphingosine kinase type 1. Compounds of the invention can be used in treatment of a range of diseases wherein increasing the level of sphingosine-1-phosphate in blood is medically indicated. Diseases that can be treated by administration of an effective dose of a compound of the invention include a neoplastic disease that involves excess vascular growth; macular degeneration or diabetic retinopathy; an allergic disease such as asthma, an inflammatory disease of the eye such as uveitis, scleritis, or vitritis; an inflammatory disease of the kidney; a fibrotic disease; atherosclerosis; or pulmonary arterial hypertension. A compound of the invention can be used to improve the integrity of a vascular barrier in a disease where the vascular barrier is disrupted, such as cancer or Alzheimer's disease.

  鞘氨醇激酶是催化鞘氨醇-1-磷酸酯生物合成的酶。该发明提供了对鞘氨醇激酶1型、鞘氨醇激酶2型或两者均具有效抑制作用的化合物。某些化合物相对于鞘氨醇激酶1型具有选择性作用于鞘氨醇激酶2型。该发明的化合物可用于治疗一系列疾病，其中增加血液中鞘氨醇-1-磷酸酯水平在医学上是指示的。通过给予该发明的化合物有效剂量可以治疗的疾病包括涉及过度血管生长的肿瘤性疾病；黄斑变性或糖尿病视网膜病变；哮喘等过敏性疾病，眼部炎症性疾病如葡萄膜炎、巩膜炎或玻璃体炎；肾脏炎症性疾病；纤维化疾病；动脉粥样硬化；或肺动脉高压。该发明的化合物可用于改善血管屏障的完整性，在血管屏障受损的疾病中，如癌症或阿尔茨海默病。
• Process for the preparation of 2-aminoalkane-1,3-diols
  申请人：L'Oreal

  公开号：US05648544A1

  公开（公告）日：1997-07-15

  A process for the preparation of 2-aminoalkane-1,3-diols by a single step reduction of alkyl 2-oximino-3-oxoalkanoates. The reduction is carried out in the presence of at least one hydride, in a solvent, under inert atmosphere and at a controlled initial temperature. Synthetic yields are markedly improved.

  一种通过单步还原烷基2-氧代亚胺-3-酮酸酯制备2-氨基烷基-1,3-二醇的方法。在惰性气氛下，在溶剂中，在控制的初始温度下，至少一种氢化物存在的情况下进行还原。合成产率显著提高。
• [EN] SPHINGOSINE KINASE INHIBITOR AMIDOXIME PRODRUGS<br/>[FR] PROMÉDICAMENTS D'AMIDOXINE INHIBITEURS DE LA SPHINGOSINE KINASE
  申请人：THORPE STEVEN BRANDON

  公开号：WO2017172989A1

  公开（公告）日：2017-10-05

  Sphingosine kinases are enzymes that catalyze the biosynthesis of sphingosine-1-phosphate. The invention provides prodrugs of compounds that are effective for inhibition of sphingosine kinase type 1, sphingosine kinase type 2, or both, according to formula (I) as described herein. Formula I compounds are useful in the treatment of a range of diseases wherein increasing the level of sphingosine-1-phosphate in blood is medically indicated. The invention also provides pharmaceutical compositions of Formula I compounds.

  鞘氨醇激酶是催化鞘氨醇-1-磷酸酯生物合成的酶。本发明提供了根据本文所述的公式(I)有效抑制鞘氨醇激酶1型、鞘氨醇激酶2型或两者的化合物的前药。公式I化合物在治疗一系列疾病中是有用的，其中在血液中增加鞘氨醇-1-磷酸酯水平在医学上是指示的。本发明还提供了公式I化合物的药物组合物。
• [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。
• [EN] SYNTHETIC METHODS FOR THE LARGE SCALE PRODUCTION FROM GLUCOSE OF ANALOGS OF SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYL CERAMIDES, AND GLYCOSYL PHYTOSPHINGOSINE<br/>[FR] METHODES DE SYNTHESE PERMETTANT LA PRODUCTION A GRANDE ECHELLE A PARTIR DE GLUCOSE D'ANALOGUES DE SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYLCERAMIDES, ET GLYCOSYLE PHYTOSPHINGOSINE
  申请人：BUNDLE DAVID R

  公开号：WO2003101937A1

  公开（公告）日：2003-12-11

  Synthetic methods are disclosed for the production from glucose of analogs of sphingosine, azidosphingosine, ceramides, lactosyl ceramides, glycosyl phytosphingosine, and enantiomeric derivatives of phytosphingosine and/or its homologues, for use in pharmaceutical applications. The disclosed syntheses are simple, direct and easily scaled.

  揭示了一种从葡萄糖生产类似物的合成方法，包括鞘氨醇、偶氮鞘氨醇、酰胺、乳糖基酰胺、糖基植物鞘氨醇以及植物鞘氨醇及/或其同系物的对映体衍生物，用于药物应用。所揭示的合成方法简单、直接且易于扩展。