(R)-2-amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride | 1596-64-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基醇类衍生物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-2-amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride
• 英文别名: 2-(R)-amino-3-(1H-imidazol-4(5)-yl)propanol dihydrochloride；R-(+)-4-(2-Amino-3-hydroxypropyl)-imidazol-dihydrochlorid；histidinol dihydrochloride；(R)-2-amino-3-(1(3)H-imidazol-4-yl)-propan-1-ol; dihydrochloride；(R)-2-Amino-3-(1(3)H-imidazol-4-yl)-propan-1-ol; Dihydrochlorid
• CAS: 1596-64-1；75614-84-5；120612-44-4
• 化学式: C₆H₁₁N₃O*2ClH
• 分子量: 214.095
• InChiKey: IQIDPEXUQGHICQ-NUBCRITNSA-N

物化性质

• 熔点：
  198-201 °C (dec.)(lit.)
• 比旋光度：
  -3 º (C=2, H2O 24 ºC)
• 溶解度：
  DMSO（少量）、甲醇（少量）、水（少量）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.93
• 氢给体数：
  3.0
• 氢受体数：
  3.0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933290090
• 危险品运输编号：
  UN 2735
• RTECS号：
  NI8260000
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

SDS

Name:	D-(+)-Histidinol dihydrochloride Material Safety Data Sheet
Synonym:	(R)-2-Amino-3-(4-imidazolyl)propanol dihydrochlorid
CAS:	75614-84-5

Section 1 - Chemical Product MSDS Name:D-(+)-Histidinol dihydrochloride Material Safety Data Sheet
Synonym:(R)-2-Amino-3-(4-imidazolyl)propanol dihydrochlorid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
75614-84-5	D-(+)-Histidinol dihydrochloride		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 75614-84-5: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 198-200 deg C (Dec.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C6H11N3O.2HCl
Molecular Weight: 214.1

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 75614-84-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
D-(+)-Histidinol dihydrochloride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 75614-84-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 75614-84-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 75614-84-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，L-Histidinol dihydrochloride 是一种与必需氨基酸 L-组氨酸具有相似结构的化合物。它作为蛋白质合成的可逆抑制剂，在培养中的非致癌性和致癌性细胞中引发不同的反应。

反应信息

• 作为反应物：
  描述：

  (R)-2-amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride 在 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  咪唑基配体支持的铜（I）配合物的酪氨酸酶和邻苯二酚氧化酶活性：结构-反应性相关性。

  摘要：

  四个基于咪唑的新配体，4-（（（1H-咪唑-4-基）甲基）-2-苯基-4,5-二氢氧基唑（L OL 1），4-（（1H-咪唑-4-基）甲基）-2-（叔丁基）-4,5-二氢唑（L OL 2），4-（（（1H-咪唑-4-基）甲基）-2-甲基-4,5-二氢唑（L OL 3）合成了N-（2,2-二甲基亚丙基）-2-（1-三苯甲基-1H-咪唑-4-基-）乙胺（L imz 1）。相应的铜（I）络合物[Cu（I）（L OL 1）（CH3CN）] PF6（CuL OL 1），[Cu（I）（L OL 2）（CH3CN）] PF6（CuL OL 2），[ Cu（I）（L OL 3）（CH3CN）] PF6（CuL OL 3），[Cu（I）（L imz 1）（CH3CN）2] PF6（CuL imz 1）以及Cu（I）络合物衍生自已知配体双（1-甲基咪唑-2-基）甲烷（BIMZ）的[Cu（I）（BIMZ）（CH3CN）]

  DOI：

  10.1007/s00775-016-1370-y
• 作为产物：
  描述：

  2-(R)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-D-histidinol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到(R)-2-amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride
  参考文献：
  名称：

  一系列新的手性组胺H3受体配体的合成和体外药理作用：2-（R和S）-氨基-3-（1H-咪唑-4（5）-基）丙基醚衍生物。

  摘要：

  为了研究组胺H3受体的立体特异性和激活机制，合成了一系列2-（R和S）-氨基-3-（1H-咪唑-4（5）-基）丙基醚衍生物。在这些化合物中，众所周知的拮抗剂碘代吡喃酮和完全激动剂R-或S-α-甲基组胺的结构结合在一个分子中。测试获得的“杂种”分子对大鼠大脑皮层的H3受体亲和力。使用大鼠脑组织切片，通过GTPγ[35S]放射自显影研究进一步筛选了一些选定的化合物的H3受体功能活性。所有合成化合物的亲和力（-log Ki = 5.9-7.9）均低于碘代吡咯芬或其两个类似物的亲和力。然而，这些化合物显示立体定向性。与R-α-甲基组胺的立体化学相似的2-氨基-3-（1H-咪唑-4（5）-基）丙基醚系列的S构型更有利。在碘代吡喃酮和类似物的丙基链中引入氨基不会改变具有芳族侧链的化合物的拮抗行为。然而，当芳族部分也被环己基取代时，该化合物表现为激动剂。这表明侧链氨基和H3-受体蛋白之间的相互作用与H3

  DOI：

  10.1021/jm980408v

文献信息

• [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION
  申请人：UNIV TEXAS

  公开号：WO2010148191A3

  公开（公告）日：2011-05-19
• Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a <i>N</i>-(2-Aminophenyl)-benzamide Binding Unit
  作者：Charles M. Marson、Christopher J. Matthews、Stephen J. Atkinson、Nermina Lamadema、N. Shaun B. Thomas

  DOI：10.1021/acs.jmedchem.5b00545

  日期：2015.9.10

  A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100 000 nM; HDAC8: IC50 = 25 000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.
• Synthesis and in Vitro Pharmacology of a Series of New Chiral Histamine H₃-Receptor Ligands:  2-(<i>R</i> and <i>S</i>)-Amino-3-(1<i>H</i>-imidazol-4(5)-yl)propyl Ether Derivatives
  作者：Jari T. Kovalainen、Johannes A. M. Christiaans、Sanna Kotisaari、Jarmo T. Laitinen、Pekka T. Männistö、Leena Tuomisto、Jukka Gynther

  DOI：10.1021/jm980408v

  日期：1999.4.1

  by a cyclohexyl group, the compounds behaved as agonists. This indicates that an interaction between the side chain amino group and the H3-receptor protein is involved in H3-receptor activation. The 2-(S)-amino-3-(1H-imidazol-4(5)-yl)propyl cyclohexylmethyl ether (23) has H3-receptor agonistic properties with high affinity for the histamine H3-receptor (-log Ki = 7.9 +/- 0.2) and might serve as a useful

  为了研究组胺H3受体的立体特异性和激活机制，合成了一系列2-（R和S）-氨基-3-（1H-咪唑-4（5）-基）丙基醚衍生物。在这些化合物中，众所周知的拮抗剂碘代吡喃酮和完全激动剂R-或S-α-甲基组胺的结构结合在一个分子中。测试获得的“杂种”分子对大鼠大脑皮层的H3受体亲和力。使用大鼠脑组织切片，通过GTPγ[35S]放射自显影研究进一步筛选了一些选定的化合物的H3受体功能活性。所有合成化合物的亲和力（-log Ki = 5.9-7.9）均低于碘代吡咯芬或其两个类似物的亲和力。然而，这些化合物显示立体定向性。与R-α-甲基组胺的立体化学相似的2-氨基-3-（1H-咪唑-4（5）-基）丙基醚系列的S构型更有利。在碘代吡喃酮和类似物的丙基链中引入氨基不会改变具有芳族侧链的化合物的拮抗行为。然而，当芳族部分也被环己基取代时，该化合物表现为激动剂。这表明侧链氨基和H3-受体蛋白之间的相互作用与H3
• Tyrosinase and catechol oxidase activity of copper(I) complexes supported by imidazole-based ligands: structure–reactivity correlations
  作者：Franziska Wendt、Christian Näther、Felix Tuczek

  DOI：10.1007/s00775-016-1370-y

  日期：2016.9

  zol-4-yl-)ethyl amine (L imz 1), have been synthesized. The corresponding copper(I) complexes [Cu(I)(L OL 1)(CH3CN)]PF6 (CuL OL 1), [Cu(I)(L OL 2)(CH3CN)]PF6 (CuL OL 2), [Cu(I)(L OL 3)(CH3CN)]PF6 (CuL OL 3), [Cu(I)(L imz 1)(CH3CN)2]PF6 (CuL imz 1) as well as the Cu(I) complex derived from the known ligand bis(1-methylimidazol-2-yl)methane (BIMZ), [Cu(I)(BIMZ)(CH3CN)]PF6 (CuBIMZ), are screened as catalysts

  四个基于咪唑的新配体，4-（（（1H-咪唑-4-基）甲基）-2-苯基-4,5-二氢氧基唑（L OL 1），4-（（1H-咪唑-4-基）甲基）-2-（叔丁基）-4,5-二氢唑（L OL 2），4-（（（1H-咪唑-4-基）甲基）-2-甲基-4,5-二氢唑（L OL 3）合成了N-（2,2-二甲基亚丙基）-2-（1-三苯甲基-1H-咪唑-4-基-）乙胺（L imz 1）。相应的铜（I）络合物[Cu（I）（L OL 1）（CH3CN）] PF6（CuL OL 1），[Cu（I）（L OL 2）（CH3CN）] PF6（CuL OL 2），[ Cu（I）（L OL 3）（CH3CN）] PF6（CuL OL 3），[Cu（I）（L imz 1）（CH3CN）2] PF6（CuL imz 1）以及Cu（I）络合物衍生自已知配体双（1-甲基咪唑-2-基）甲烷（BIMZ）的[Cu（I）（BIMZ）（CH3CN）]