3-deshydrocarnitine | 10457-99-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-deshydrocarnitine
• 英文别名: 3-dehydrocarnitine；HMDB12154；3-oxo-4-(trimethylazaniumyl)butanoate
• CAS: 10457-99-5
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: YNOWULSFLVIUDH-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  3

SDS

Name:	Dehydrocarnitine Hydrochloride 96+% Material Safety Data Sheet
Synonym:	None Known
CAS:	10457-99-5

Section 1 - Chemical Product MSDS Name:Dehydrocarnitine Hydrochloride 96+% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10457-99-5	Dehydrocarnitine Hydrochloride	96+%	unlisted

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

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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.

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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. 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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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. 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# 10457-99-5: 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:
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: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 100 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:
Specific Gravity/Density:
Molecular Formula: C7H13NO3.HCl
Molecular Weight: 195.65

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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:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10457-99-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Dehydrocarnitine Hydrochloride - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 10457-99-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10457-99-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10457-99-5 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

反应信息

• 作为反应物：
  描述：

  3-deshydrocarnitine 在 1,4-dihydronicotinamide adenine dinucleotide 作用下， 生成 DL-肉碱
  参考文献：
  名称：

  Vandecasteele, Jean-Paul; Lemal, Jeannine, Bulletin de la Societe Chimique de France, 1980, vol. 2, # 1-2, p. 101 - 103

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-Ethoxycarbonyl-2-oxo-propyl)-trimethyl-ammonium; bromide 在 氢溴酸 作用下， 生成 3-deshydrocarnitine
  参考文献：
  名称：

  Darstellung von 3-Dehydro-carnitin

  摘要：

  DOI：

  10.1515/bchm2.1968.349.2.1310

文献信息

• PROCESS FOR THE PREPARATION OF BETAINES
  申请人：Paradies Gesa

  公开号：US20100267986A1

  公开（公告）日：2010-10-21

  Betaines of formula R 3 N + -Q-COO − (I), wherein R is C 1-4 alkyl and Q is C 1-4 alkanediyl, optionally substituted with hydroxy, are prepared in one step by adding an ω-halocarboxylate of formula X-Q-COOR′ (II), wherein Q is as defined above, R′ is C1 1-4 alkyl and X is chlorine, bromine or iodine, to an aqueous solution containing a tertiary amine of formula R 3 N (III), Wherein R is as defined above and a base selected from alkali hydroxides and alkaline earth hydroxides. The process is particularly suited to the production of L-carnitine.

  公式为R3N+-Q-COO−(I)的Betaines，其中R是C1-4烷基，Q是C1-4烷二基，可选择性地被羟基取代，通过将公式为X-Q-COOR'（II）的ω-卤代羧酸酯，其中Q如上所定义，R'是C11-4烷基，X是氯，溴或碘，加入到含有公式为R3N（III）的三级胺和碱金属氢氧化物和碱土金属氢氧化物的水溶液中的一步制备。该过程特别适用于L-肉碱的生产。
• Purification and Properties of a New Enzyme, D-Carnitine Dehydrogenase, from<i>Agrobacterium</i>sp. 525a
  作者：Siswa Setyahadi、Tomoko Ueyama、Takeshi Arimoto、Nobuhiro Mori、Yutaka Kitamoto

  DOI：10.1271/bbb.61.1055

  日期：1997.1

  A new enzyme, D-carnitine dehydrogenase from Agrobacterium sp. 525a, was purified by DEAE-Toyopearl, ammonium sulfate fractionation, Sephadex G-75, affinity chromatography, and Mono Q and TSK-gel filtration column chromatography. The enzyme had the molecular mass of 89 kDa and consisted of three identical subunits. The optimum pH for the oxidation reaction was 9.3. The Michaelis constants for D-carnitine

  一种新的酶，来自农杆菌属的D-肉碱脱氢酶。525a通过DEAE-Toyopearl，硫酸铵分级分离，Sephadex G-75，亲和色谱以及Mono Q和TSK-凝胶过滤柱色谱纯化。该酶的分子量为89 kDa，由三个相同的亚基组成。氧化反应的最佳pH为9.3。D-肉碱和NAD +的米氏常数分别为3.1和0.07 mM。对N末端的20个氨基酸进行测序。
• Purification and properties of carnitine dehydrogenase from Pseudomonas putida
  作者：Philippe Goulas

  DOI：10.1016/0167-4838(88)90222-1

  日期：1988.12

  Carnitine dehydrogenase (carnitine:NAD+ oxidoreductase, EC 1.1.1.108) from Pseudomonas putida IFP 206 catalyzes the oxidation of L-carnitine to 3-dehydrocarnitine. The enzyme was purified 72-fold to homogeneity as judged by polyacrylamide gel electrophoresis. The molecular mass of this enzyme is 62 kDa and consists of two identical subunits. The isoelectric point was found to be 4.7. the carnitine

  来自恶臭假单胞菌IFP 206的肉碱脱氢酶（肉碱：NAD +氧化还原酶，EC 1.1.1.108）催化L-肉碱氧化成3-脱氢肉碱。通过聚丙烯酰胺凝胶电泳判断，将酶纯化72倍至同质。该酶的分子量为62 kDa，由两个相同的亚基组成。发现等电点为4.7。肉碱脱氢酶对L-肉碱和NAD +具有特异性。发现在还原反应中用于氧化反应的酶活性的最佳pH为9.0和7.0。最佳温度为30摄氏度。确定了基材的Km值。
• Identification of genes required for Pseudomonas aeruginosa carnitine catabolism
  作者：Matthew J. Wargo、Deborah A. Hogan

  DOI：10.1099/mic.0.028787-0

  日期：2009.7.1

  predicted P. aeruginosa carnitine dehydrogenase homologue along with other genes required for growth on carnitine. The second region identified, PA1999-PA2000, encodes the alpha and beta subunits of a predicted 3-ketoacid CoA-transferase, an enzymic activity hypothesized to be involved in the first step of deacetylation of 3-dhc. Furthermore, we confirmed that an intact GB catabolic pathway is required

  肉碱是一种普遍存在于动物组织中的季胺化合物，是病原体感染过程中潜在的碳、氮和能量来源。铜绿假单胞菌细胞裂解物中的活性表征先前表明，肉碱转化为 3-脱氢肉碱 (3-dhc)，后者又代谢为甘氨酸甜菜碱 (GB)，这是肉碱分解代谢为甘氨酸的中间代谢物。然而，肉碱分解代谢所需的酶的身份尚不清楚。我们使用铜绿假单胞菌 PA14 转座子突变体库的遗传筛选来鉴定肉碱生长所需的基因。我们确定了肉碱分解代谢所需的两个基因组区域及其相邻的转录调节因子。PA5388-PA5384 区域包含预测的 P。铜绿肉碱脱氢酶同系物以及在肉碱上生长所需的其他基因。确定的第二个区域 PA1999-PA2000 编码预测的 3-酮酸 CoA 转移酶的 α 和β 亚基，该酶活性被假设为参与 3-dhc 脱乙酰化的第一步。此外，我们证实在肉碱上生长需要完整的 GB 分解代谢途径。PA5389 和 PA1998 转录因子是在肉碱上生长所必需的。PA5389
• Revealing the hidden functional diversity of an enzyme family
  作者：Karine Bastard、Adam Alexander Thil Smith、Carine Vergne-Vaxelaire、Alain Perret、Anne Zaparucha、Raquel De Melo-Minardi、Aline Mariage、Magali Boutard、Adrien Debard、Christophe Lechaplais、Christine Pelle、Virginie Pellouin、Nadia Perchat、Jean-Louis Petit、Annett Kreimeyer、Claudine Medigue、Jean Weissenbach、François Artiguenave、Véronique De Berardinis、David Vallenet、Marcel Salanoubat

  DOI：10.1038/nchembio.1387

  日期：2014.1

  Enzyme annotations often suffer from incomplete functional information for homologous sequences. Extrapolation from one characterized enzyme to multiple possible substrate-enzyme pairs, using bioinformatics and experimental approaches, leads to four distinct β-keto acid cleavage enzyme functional motifs and assignment of 14 new activities. Millions of protein database entries are not assigned reliable functions, preventing the full understanding of chemical diversity in living organisms. Here, we describe an integrated strategy for the discovery of various enzymatic activities catalyzed within protein families of unknown or little known function. This approach relies on the definition of a generic reaction conserved within the family, high-throughput enzymatic screening on representatives, structural and modeling investigations and analysis of genomic and metabolic context. As a proof of principle, we investigated the DUF849 Pfam family and unearthed 14 potential new enzymatic activities, leading to the designation of these proteins as β-keto acid cleavage enzymes. We propose an in vivo role for four enzymatic activities and suggest key residues for guiding further functional annotation. Our results show that the functional diversity within a family may be largely underestimated. The extension of this strategy to other families will improve our knowledge of the enzymatic landscape.

  酶注释通常会因同源序列的功能信息不完整而受到影响。利用生物信息学和实验方法，从一种已知的酶推断出多种可能的底物-酶对，从而发现了四种不同的β-酮酸裂解酶功能基序，并确定了14种新酶的活性。数百万条蛋白质数据库条目没有可靠的酶功能，这阻碍了对生物体化学多样性的全面理解。在此，我们描述了一种综合策略，用于发现未知或鲜为人知的蛋白质家族中催化各种酶活性的酶。该方法依赖于定义家族中保守的通用反应，对代表性酶进行高通量筛选，进行结构和建模研究，以及分析基因组和代谢背景。作为原理验证，我们研究了DUF849 Pfam家族，并发现了14种潜在的新酶活性，从而将这些蛋白质指定为β-酮酸裂解酶。我们提出了四种酶活性的体内作用，并提出了关键残基，以指导进一步的功能注释。我们的结果表明，一个家族内的功能多样性可能被大大低估了。将这一策略扩展到其他家族将提高我们对酶谱的认识。