8-苄基茶碱 | 2879-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 8-苄基茶碱
• 英文名称: 8-benzyltheophylline
• 英文别名: 8-Benzyltheophyllin；8-benzyl-1,3-dimethyl-7H-purine-2,6-dione
• CAS: 2879-15-4
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: SWKGFZTXWQMFLK-UHFFFAOYSA-N

物化性质

• 熔点：
  298-300℃
• 沸点：
  556.5±52.0 °C(Predicted)
• 密度：
  1.335
• 溶解度：
  可溶于DMSO（略微加热）、甲醇（略微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  2-8℃

SDS

Name:	8-Benzyltheophylline 99% Material Safety Data Sheet
Synonym:	1H-Purine-2,6-Dione; 3,7-Dihydro-1,3-Dimethyl-8-(Phenylmethyl)-
CAS:	2879-15-4

Section 1 - Chemical Product MSDS Name:8-Benzyltheophylline 99% Material Safety Data Sheet
Synonym:1H-Purine-2,6-Dione; 3,7-Dihydro-1,3-Dimethyl-8-(Phenylmethyl)-

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2879-15-4	8-Benzyltheophylline	99	220-725-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

---

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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 2879-15-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: very slightly yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 292 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density:
Molecular Formula: C14H14N4O2
Molecular Weight: 270.27

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2879-15-4: XH4791000 LD50/LC50:
Not available.
Carcinogenicity:
8-Benzyltheophylline - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 2879-15-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2879-15-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2879-15-4 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：用作医药中间体

反应信息

• 作为反应物：
  描述：

  8-苄基茶碱 生成 7-[2-[乙基(2-羟基乙基)氨基]乙基]-3,7-二氢-1,3-二甲基-8-(苯甲基)-1H-嘌呤-2,6-二酮
  参考文献：
  名称：

  Process for converting a xanthine ring or xanthine ring derivatives into

  摘要：

  本发明涉及一种制备巴米费林或依他米费林的过程，其中混合物包括：a）茶碱或8-苄基茶碱；b）烷基二卤代物；和c）摩尔过量的胺，在弱碱存在下反应，反应在温度高于90℃并在高于10^5的压力下进行。

  公开号：

  US05739331A1
• 作为产物：
  描述：

  N-(6-氨基-1,2,3,4-四氢-1,3-二甲基-2,4-二氧代-嘧啶-5-基)-2-苯基-乙酰胺 在 sodium hydroxide 作用下， 生成 8-苄基茶碱
  参考文献：
  名称：

  Kostolansky et al., Chemicke Zvesti, 1956, vol. 10, p. 96,106

  摘要：

  DOI：

文献信息

• Dual inhibition of monoamine oxidase B and antagonism of the adenosine A2A receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues
  作者：Judey Pretorius、Sarel F. Malan、Neal Castagnoli、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2008.07.088

  日期：2008.9

  The adenosine A(2A) receptor has emerged as an attractive target for the treatment of Parkinson's disease (PD). Evidence suggests that antagonists of the A(2A) receptor (A(2A) antagonists) may be neuroprotective and may help to alleviate the symptoms of PD. We have reported recently that several members of the (E)-8-styrylcaffeine class of A(2A) antagonists also are potent inhibitors of monoamine oxidase

  腺苷A（2A）受体已成为治疗帕金森氏病（PD）的有吸引力的靶标。有证据表明，A（2A）受体拮抗剂（A（2A）拮抗剂）可能具有神经保护作用，并可能有助于减轻PD的症状。我们最近报道，（E）-8-苯乙烯基咖啡因类别的A（2A）拮抗剂的几个成员也是单胺氧化酶B（MAO-B）的有效抑制剂。由于已知MAO-B抑制剂具有抗帕金森氏症的特性，因此阻断MAO-B和A（2A）受体的双重靶标定向药物在PD的管理中可能具有更高的价值。为了进一步探索这个概念，我们准备了三类其他的C-8取代咖啡因类似物。选择时，8-苯基和8-苄基咖啡因基类似物显示出相对较弱的MAO-B抑制能力（E，发现E）-8-（4-苯基丁二烯-1-基）咖啡因基类似物是异常有效的可逆MAO-B抑制剂，其酶抑制剂解离常数（K（i）值）为17至149 nM。此外，这些（E，E）-8-（4-苯基丁二烯-1-基）咖啡因可作为有效的A（2A）拮抗剂，其K（i）值为59至153
• 7-(3-Substituted amino-2-hydroxypropyl)-8-benzyl-, or -8-phenyltheophyllines
  作者：Ladislav Štibrányi、Alfonz Rybár、Ján Jendrichovský、Lýdia Boženková、Vladimír Kovalčík

  DOI：10.1135/cccc19821339

  日期：——

  N-Substituted derivatives of 7-(3-amino-2-hydroxypropyl)-8-benzyl- (V), or -8-phenyltheophylline (VI) were prepared by addition of the appropriate amines to 7-epoxypropyl-8-benzyl- (III), or -8-phenyltheophyllines (IV). Compounds III and IV were obtained by alkylation of 8-benzyl-, or 8-phenyltheophyllines with 1-chloro-2,3-epoxypropane. DerivativesV and VI exhibited a peripheral vasodilatation effect in vitro.

  将7-(3-氨基-2-羟基丙基)-8-苄基-（V），或8-苯基茶碱（VI）的N-取代衍生物通过将适当的胺添加到7-环氧丙基-8-苄基-（III），或8-苯基茶碱（IV）中制备。化合物III和IV是通过用1-氯-2,3-环氧丙烷烷基化8-苄基-或8-苯基茶碱而获得的。衍生物V和VI在体外表现出外周血管扩张作用。
• Concise Xanthine Synthesis through a Double-Amidination Reaction of a 6-Chlorouracil with Amidines using Base-Metal Catalysis
  作者：Bénédicte Morel、Philippe Franck、Johan Bidange、Sergey Sergeyev、Dan A. Smith、Jonathan D. Moseley、Bert U. W. Maes

  DOI：10.1002/cssc.201601483

  日期：2017.2.8

  A new and concise route towards xanthines through a double‐amidination reaction is described; consecutive intermolecular C−Cl and intramolecular oxidative C−H amidination. N‐uracil amidines are obtained through SNAE on a 6‐chlorouracil with amidines. Direct Cu‐catalyzed oxidative C−H amidination on these N‐uracil amidines yields polysubstituted xanthines. Sustainable oxidants, tBu2O2 or O2, can be

  描述了通过双酰胺化反应制备黄嘌呤的新的简洁途径。连续的分子间C-Cl和分子内氧化性CH-H酰胺化。Ñ尿嘧啶脒通过S取得Ñ AE在6氯尿嘧啶与脒。在这些N-尿嘧啶am上直接进行Cu催化的氧化CH H酰胺化反应可得到多取代的黄嘌呤。可持续的氧化剂t Bu 2 O 2或O 2可用于该氧化酶类型的反应。该协议允许引入N 1，N 3，N 7和C在黄嘌呤骨架结构中有8个取代基，从而避免了后功能化步骤。6-氯尿嘧啶和am很容易从市场上购买或通过合成获得。
• Low glycemic response compositions
  申请人：The Procter & Gamble Co.

  公开号：US20020187219A1

  公开（公告）日：2002-12-12

  The present disclosure is related to compositions useful in the field of foods and beverages. In particular, the present invention relates to those compositions that reduce the postprandial rise in blood glucose (described as low Glycemic Index) that synergistically provide enhanced metabolism in the mammalian system and inhibit the storage of systemic fat. In particular, the present invention relates to compositions comprising: a) one or more flavanols; b) one or more bracers; and c) vitamin B; wherein the composition exhibits a Glycemic Index of about 55 or less. As disclosed, the unique combination of ingredients, which provide the defined, low Glycemic Index, work synergistically together to enhance perception of energy and/or improve physiological energy via metabolism enhancement over a long duration of time, without resulting in sudden peaks of glucose in the mammalian system. Thus, the present compositions effectively modulate glucose in the system, thereby providing energy to the system without resulting in the storage of systemic fat.

  本公开涉及在食品和饮料领域有用的组合物。特别是，本发明涉及那些能够减少餐后血糖上升（描述为低升糖指数）的组合物，这些组合物在哺乳动物系统中协同作用，提供增强的代谢作用并抑制系统性脂肪的储存。特别是，本发明涉及包括：a）一种或多种黄烷醇；b）一种或多种支链氨基酸；和c）维生素B的组合物；其中该组合物表现出约55或更低的升糖指数。如本文所述，这些独特的成分组合，以定义的低升糖指数为特征，协同作用，能够提高能量感知和/或通过代谢增强长时间改善生理能量，而不会导致哺乳动物系统中的血糖突然峰值。因此，本组合物有效地调节系统中的葡萄糖，从而为系统提供能量而不导致系统性脂肪的储存。
• Compositions, kits, and methods for promoting defined health benefits
  申请人：——

  公开号：US20030069202A1

  公开（公告）日：2003-04-10

  The present invention is directed to compositions comprising: (a) a first component selected from the group consisting of gelatin, cartilage, aminosugars, glycosaminoglycans, methylsulfonylmethane, precursors of methylsulfonylmethane, S-adenosylmethionine, salts thereof, and mixtures thereof; and (b) a second component comprising: (i) a cation source selected from the group consisting of calcium, potassium, magnesium, and mixtures thereof; and (ii) an edible acid source. The present invention is further directed to food, beverage, pharmaceutical, over-the- counter, and dietary supplement products, which comprise the present compositions. The invention also relates to kits comprising the present compositions and information that use of the composition promotes one or more of the presently defined health benefits, including joint health, bone health, cardiac health, and anti-inflammation. The present invention additionally relates to methods of treating joint function, bone function, cardiac function, or inflammation comprising administering to a mammal a composition as defined herein.

  本发明涉及包括以下组分的组合物：(a)从明胶、软骨、氨基糖、糖胶质、甲基磺酰甲烷、甲基磺酰甲烷的前体、S-腺苷甲硫氨酸、其盐和其混合物中选择的第一组分; 和(b)包括：(i)从钙、钾、镁和其混合物中选择的阳离子源; 和(ii)可食用的酸源的第二组分。本发明还涉及包含本组合物的食品、饮料、制药、非处方药和膳食补充剂产品。本发明还涉及包含本组合物和使用该组合物促进当前定义的健康益处之一或多个的信息的套件。本发明还涉及治疗关节功能、骨功能、心脏功能或炎症的方法，包括向哺乳动物投与本文所定义的组合物。