2,3-戊二酮 | 600-14-6

• 物质功能分类: 香精与香料 - 合成香料 - 酮类香料
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,3-戊二酮
• 中文别名: 2,3-戊烷二酮；乙酰丙酰；乙酰基丙酰
• 英文名称: 2,3-Pentanedione
• 英文别名: pentane-2,3-dione；pentan-2,3-dione；ethyl methyl diketone
• CAS: 600-14-6
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: TZMFJUDUGYTVRY-UHFFFAOYSA-N

物化性质

• 熔点：
  -52 °C (lit.)
• 沸点：
  110-112 °C (lit.)
• 密度：
  0.957 g/mL at 25 °C (lit.)
• 闪点：
  66 °F
• 溶解度：
  水中的溶解度为60克/升
• 暴露限值：
  NIOSH: TWA 9.3 ppb; STEL 31 ppb
• LogP：
  -0.85
• 物理描述：
  Liquid
• 颜色/状态：
  Yellow liquid
• 气味：
  Somewhat sweet odor similar to quinone ... Detection: 20 ppb. Aroma characteristics at 1.0%: buttery diacytl-like, fermented dairy and creamy, popcorn buttery
• 味道：
  Penetrating buttery taste on dilution...Taste characteristics at 1 to 5 ppm: sweet buttery, creamy, cheesy, slightly toasted dairy, with a rich baked goods nuance and good mouth feel
• 蒸汽压力：
  2.67 kPa at 20 °C /20.0 mm Hg at 20 °C/
• 稳定性/保质期：
  1. **性质与稳定性**：在常温常压下，该物质不会分解。 2. 黄色液体，广泛存在于多种食品和饮品中，如家禽、家畜奶乳、焙烤类坚果、炸土豆、面包、浆果、番茄、饮料的可可、茶叶以及酒精饮料中的啤酒和各种洋酒。某些精油也含有此成分。该化合物属于丁二酮类似系列产品，具有明显的乳脂奶香风味，并且能溶于水并带有微甜的味道。 3. 该物质还存在于主流烟气中。
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 折光率：
  Index of refraction: 1.4014 at 19 °C
• 保留指数：
  660;666;669;681;665;662;664;650;668;662;674;675;667;660;675;665;665;681;668.7;678.1;680;668;672;664;674;662;664;673;674;651;652;673;674;681;663;681;673;676;681;678.1;675.8

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

我们开发了一个系统，用于将培养的人体支气管/气管上皮细胞（NHBEs）暴露于调味蒸气中。NHBEs暴露于二乙酰或2,3-戊二酮蒸气中6小时（25或大于/等于60 ppm）...对基底外侧介质的分析表明，NHBEs将二乙酰和2,3-戊二酮分别代谢为乙偶姻和2-羟基-3-戊酮。

We developed a system to expose cultured human bronchial/tracheal epithelial cells (NHBEs) to flavoring vapors. NHBEs were exposed for 6 hr to diacetyl or 2,3-pentanedione vapors (25 or >/= 60 ppm)... Analysis of the basolateral medium indicated that NHBEs metabolize diacetyl and 2,3-pentanedione to acetoin and 2-hydroxy-3-pentanone, respectively.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：2,3-戊二酮是一种黄色液体。它被用作调味剂（黄油风味），包括许多电子烟品牌。人类暴露和毒性：微波爆米花行业的工人吸入黄油风味可能导致“爆米花工人肺”。将培养的人支气管/气管上皮细胞（NHBEs）暴露于二乙酰或2,3-戊二酮蒸气（25或≥60 ppm）6小时，并测量对短路电流和跨上皮电阻（Rt）的影响。暴露于25 ppm后，两种风味剂立即减少了Na+的传输，而不影响Cl-的传输或Na+,K+-泵的活动。据报道，二乙酰和2,3-戊二酮的浓度（100-360 ppm）在体内引起上皮损伤，而60 ppm导致NHBEs在暴露后0小时死亡。结果表明，与体内或体外细胞形态变化的浓度相比，较低浓度的风味剂暂时抑制了气道上皮细胞的离子传输。动物研究：大鼠吸入空气，2,3-戊二酮（112、241、318或354 ppm）6小时后次日处死。吸入2,3-戊二酮的大鼠发展为坏死性鼻炎、气管炎和支气管炎。为了研究延迟毒性，另外一组大鼠吸入318（范围317.9-318.9）ppm 2,3-戊二酮6小时，在暴露后0至2、12至14或18至20小时处死。上鼻呼吸上皮损伤涉及凋亡和坏死，在暴露后12至14小时进展。嗅觉神经上皮损伤包括与支撑细胞相比，表达2,3-戊二酮代谢酶的二碳/L-木糖还原酶减少的嗅觉神经元的丢失。半胱天冬酶3激活偶尔涉及在嗅球（OB）突触的嗅觉神经束。另一组大鼠吸入270 ppm 2,3-戊二酮6小时41分钟后，使用实时PCR观察到嗅球、纹状体、海马和脑桥中的IL-6和一氧化氮合酶-2表达增加，血管内皮生长因子A表达减少。紧密蛋白-1在嗅球和纹状体的表达增加。在另一实验中，雄性和雌性大鼠和小鼠每天暴露于0、50、100或200 ppm 2,3-戊二酮6小时，每周5天，最多2周。在1、3、5和10次暴露后收集支气管肺泡灌洗液（BALF），在12次暴露后评估组织病理学。在5天和10天暴露于200 ppm的大鼠BALF中，MCP-1、MCP-3、CRP、FGF-9、纤维蛋白原和OSM增加了2至9倍。在小鼠中，仅在暴露于200 ppm 5天后纤维蛋白原增加。在所有暴露于200 ppm的大鼠和小鼠中，呼吸道上皮是毒性的部位。值得注意的是，2,3-戊二酮还引起了大鼠的腔内和壁内纤维化气道病变。在第三个实验中，暴露于150或200 ppm 2,3-戊二酮的大鼠发展为支气管纤维化。在小鼠中，当测试浓度高达50%时，2,3-戊二酮不是皮肤刺激物。然而，在暴露于2,3-戊二酮后，观察到小鼠淋巴细胞的浓度依赖性增加。

IDENTIFICATION AND USE: 2,3-Pentanedione is a yellow liquid. It is used as flavoring agent (butter flavoring) including many e-cigarette brands. HUMAN EXPOSURE AND TOXICITY: Inhalation of butter flavoring by workers in the microwave popcorn industry may result in "popcorn workers' lung." Cultured human bronchial/tracheal epithelial cells (NHBEs) were exposed for 6 hours to diacetyl or 2,3-pentanedione vapors (25 or >/= 60 ppm) and the effects on short circuit current and transepithelial resistance (Rt) were measured. Immediately after exposure to 25 ppm both flavorings reduced Na+ transport, without affecting Cl- transport or Na+,K+-pump activity. Concentrations (100-360 ppm) of diacetyl and 2,3-pentanedione reported to give rise in vivo to epithelial damage, and 60 ppm, caused death of NHBEs 0 hours post-exposure. The results indicate that ion transport is inhibited transiently in airway epithelial cells by lower concentrations of the flavorings than those that result in morphological changes of the cells in vivo or in vitro. ANIMAL STUDIES: Rats that inhaled air, 2,3-pentanedione (112, 241, 318, or 354 ppm) for 6 hours were sacrificed the following day. Rats inhaling 2,3-pentanedione developed necrotizing rhinitis, tracheitis, and bronchitis. To investigate delayed toxicity, additional rats inhaled 318 (range, 317.9-318.9) ppm 2,3-pentanedione for 6 hours and were sacrificed 0 to 2, 12 to 14, or 18 to 20 hours after exposure. Respiratory epithelial injury in the upper nose involved both apoptosis and necrosis, which progressed through 12 to 14 hours after exposure. Olfactory neuroepithelial injury included loss of olfactory neurons that showed reduced expression of the 2,3-pentanedione-metabolizing enzyme, dicarbonyl/L-xylulose reductase, relative to sustentacular cells. Caspase 3 activation occasionally involved olfactory nerve bundles that synapse in the olfactory bulb (OB). An additional group of rats inhaling 270 ppm 2,3-pentanedione for 6 hours 41 minutes showed increased expression of IL-6 and nitric oxide synthase-2 and decreased expression of vascular endothelial growth factor A in the OB, striatum, hippocampus, and cerebellum using real-time PCR. Claudin-1 expression increased in the OB and striatum. In other experiment, male and female rats and mice were exposed to 0, 50, 100, or 200 ppm 2,3-pentanedione 6 hr/d, 5 d/wk for up to 2 weeks. Bronchoalveolar lavage fluid (BALF) was collected after 1, 3, 5, and 10 exposures, and histopathology was evaluated after 12 exposures. MCP-1, MCP-3, CRP, FGF-9, fibrinogen, and OSM were increased 2- to 9-fold in BALF of rats exposed for 5 and 10 days to 200 ppm. In mice, only fibrinogen was increased after 5 exposures to 200 ppm. The epithelium lining the respiratory tract was the site of toxicity in all mice and rats exposed to 200 ppm. Significantly, 2,3-pentanedione also caused both intraluminal and intramural fibrotic airway lesions in rats. In third experiment, rats exposed to 150 or 200 ppm 2,3-pentanedione developed bronchial fibrosis. In mice, 2,3-pentanedione was not a dermal irritant when tested at concentrations up to 50%. However, concentration-dependent increases in lymphocyte proliferation were observed following exposure to 2,3-pentanedione in mice.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

/SRP:/ 紧急急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧卧位（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入性肺炎。保持患者安静，维持正常体温。寻求医疗帮助。

/SRP:/ Immediate First Aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。必要时进行吸痰。观察呼吸不足的迹象，必要时协助通气。通过非重复呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时治疗……。对于污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的咳嗽反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……。/酮体及其相关化合物/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . For contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Ketones and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊阀面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用丙美卡因氢氯化物协助眼部冲洗……。/酮体及相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  F
• 安全说明：
  S16,S26,S36,S37/39
• 危险类别码：
  R36/37/38,R11
• WGK Germany：
  1
• 海关编码：
  2914190090
• 危险品运输编号：
  UN 1224 3/PG 2
• 危险类别：
  3
• RTECS号：
  SA1850000
• 包装等级：
  II
• 危险性防范说明：
  P210,P305+P351+P338
• 危险性描述：
  H225,H315,H319
• 储存条件：
  贮存：将密器密封后，储存在密封的主藏器中，并放置于阴凉、干燥处。

SDS

Name:	2 3-Pentanedione 97% Material Safety Data Sheet
Synonym:	Acetylpropiony
CAS:	600-14-6

Section 1 - Chemical Product MSDS Name:2 3-Pentanedione 97% Material Safety Data Sheet
Synonym:Acetylpropiony

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
600-14-6	2,3-Pentanedione	97	209-984-8

Hazard Symbols: F
Risk Phrases: 11

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable.
Potential Health Effects
Eye:
May cause eye irritation and possible burns.
Skin:
Causes skin irritation and possible burns.
Ingestion:
May cause digestive tract disturbances.
Inhalation:
May cause respiratory tract irritation. Vapors may cause dizziness or suffocation.
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 immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Water may be ineffective. Do NOT use straight streams of water. Cool containers with flooding quantities of water until well after fire is out.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. A vapor suppressing foam may be used to reduce vapors. Water spray may reduce vapor but may not prevent ignition in closed spaces.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a cool, dry, well-ventilated area away from incompatible substances. Refrigerator/flammables. Keep containers tightly closed.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 600-14-6: 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: Liquid
Color: clear yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 110.0 - 112.0 deg C
Freezing/Melting Point: -52 deg C
Autoignition Temperature: Not available.
Flash Point: 18 deg C ( 64.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: partially soluble
Specific Gravity/Density: .9570g/cm3
Molecular Formula: C5H8O2
Molecular Weight: 100.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 600-14-6: SA1850000 LD50/LC50:
CAS# 600-14-6: Draize test, rabbit, skin: 500 mg/24H Moderate; Oral, rat: LD50 = 3 gm/kg; Skin, rabbit: LD50 = >2500 mg/kg.
Skin, Rabbitt:LD50 = >2500 Carcinogenicity:
2,3-Pentanedione - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Shipping Name: FLAMMABLE LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1993
Packing Group: II
IMO
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3.2
UN Number: 1993
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3
UN Number: 1993
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F
Risk Phrases:
R 11 Highly flammable.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 33 Take precautionary measures against static
discharges.
S 50A Do not mix with acids.
WGK (Water Danger/Protection)
CAS# 600-14-6: 1
Canada
CAS# 600-14-6 is listed on Canada's DSL List.
CAS# 600-14-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 600-14-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

2,3-戊二酮为黄绿色油状液体，具有甜白脱、奶油、焦糖香气，并带有坚果底香。其微溶于水，易溶于乙醇等有机溶剂，能发生二聚、氧化、还原、加成、缩合反应。可被高锰酸钾分解，与氢氧化钠作用转化为α-羟基酸。

用途 2,3-戊二酮可用作食品香精的香料、明胶硬化剂和相片的黏结剂等。我国GB 2760-86规定其为允许使用的食用香料，主要用于配制巧克力和奶油型香精。天然存在于咖啡、啤酒、老姆酒、威士忌、红葡萄酒、白葡萄酒中，也存在于芬兰松的精油中。

含量分析 按醛和酮测定法（OT-7）中的方法一（羟胺法）测定，所取试样量为400mg。计算中的当量因子（e）取25.03。或按气相色谱法（GT-10-4）中用非极性柱的方法测定。

毒性 GRAS（FEMA）。

使用限量 FEMA（mg/kg）：软饮料0.60；冷饮3.3；糖果5.9；焙烤食品9.6；布丁类0.28；裱花层0.30。适度为限（FDA§172．515，2000）。

最大允许使用量与残留标准 根据GB 2760--1996规定，2,3-戊二酮作为食品用香料的最大允许使用量和最大允许残留量应不超过GB 2760中的标准。主要用于配制巧克力和奶油型香精。

生产方法 天然存在于芬兰松等精油中。人工合成可在盐酸羟胺存在下，于氮气保护下，用过量亚硝酸钠和稀盐酸使甲基丙酮氧化而成。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3,4-己二酮	3,4-hexanedione	4437-51-8	C6H10O2	114.144
  2-戊酮	2-Pentanone	107-87-9	C5H10O	86.1338
  3-戊酮	pentan-3-one	96-22-0	C5H10O	86.1338

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  庚烷-3,4-二酮	heptane-3,4-dione	13706-89-3	C7H12O2	128.171
  2-戊酮	2-Pentanone	107-87-9	C5H10O	86.1338
  3-戊酮	pentan-3-one	96-22-0	C5H10O	86.1338
  辛烷-3,4-二酮	octane-3,4-dione	3457-39-4	C8H14O2	142.198

反应信息

• 作为反应物：
  描述：

  2,3-戊二酮 在 一水合肼 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 3,5-二甲基吡唑
  参考文献：
  名称：

  Synthesis for 7-alkylamino-3-methylpyrazolo [4,3-d]pyrimidines

  摘要：

  公开了一种改进的合成方法，用于合成已知为强效细胞分裂素拮抗剂的7-烷基氨基-3-甲基吡唑并[4,3-d]嘧啶。

  公开号：

  US04282361A1
• 作为产物：
  描述：

  3-氯-3-(乙硫基)-2-戊酮 在 水 、 sodium carbonate 、 mercury dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2,3-戊二酮
  参考文献：
  名称：

  α-二酮，α，α-二烷氧基酮和α-烷氧基-α-亚磺酰基化酮的区域专一性合成

  摘要：

  通过汞诱导的区域特异性形成的α-氯代-α-（烷硫基）酮的溶剂化反应，开发了一种方便的合成α-二酮及其单保护缩醛，即α-酮缩醛的方法。类似地，当α-氯-α-亚磺酰基化的酮与碱性醇介质反应时，形成α-烷氧基-α-亚磺酰基化的酮。α-烷氧基-α-亚磺酰化的酮本身可以转化为α-二酮或α-酮缩醛，然后在无水条件下将其水解为相应的α-二酮。

  DOI：

  10.1016/s0040-4020(00)00604-9
• 作为试剂：
  描述：

  2-溴苯甲酸 在 2,3-戊二酮 、 copper(ll) bromide sodium carbonate 、 水 、 盐酸 作用下， 以 水 为溶剂， 反应 17.0h， 以94%的产率得到水杨酸
  参考文献：
  名称：

  Process for the synthesis of hydroxy aromatic acids

  摘要：

  在含有铜源和配位于铜的配体的反应混合物中，从卤代芳香酸中高产率和高纯度（> 95％）地产生羟基芳香酸。

  公开号：

  US07351856B1

文献信息

• Synthesis and Characterisation of Indium(III) Bis-Thiosemicarbazone Complexes: 18F Incorporation for PET Imaging
  作者：Taracad K. Venkatachalam、Paul V. Bernhardt、Gregory K. Pierens、Damion H. R. Stimson、Rajiv Bhalla、David C. Reutens

  DOI：10.1071/ch18559

  日期：——

  coordination sphere in all indium complexes. In some complexes, an intermolecular hydrogen bond was present between the chlorine atom and an NH group. Three different indium chlorido complexes were converted into the corresponding fluorido-derivative by a simple halide exchange method using K18F. These novel complexes, containing the positron emitting isotope 18F, may have potential applications in positron

  使用甲醇钠的甲醇溶液，从适当取代的双硫代半氨基甲酮开始，制备了几种双硫代半氨基甲酮的与铟相关的氯配合物。进行了详细的NMR研究以指定结构，包括COSY，HSQC和HMBC技术。所有铟配合物的结构均使用单晶X射线衍射解析。氯配体存在于所有铟配合物中的方形锥体配位球的顶点。在一些配合物中，在氯原子和NH基团之间存在分子间氢键。通过使用K 18的简单卤化物交换方法，将三种不同的铟氯离子络合物转化为相应的氟代衍生物F.包含正电子发射同位素18 F的这些新型复合物，可能在正电子发射断层扫描（PET）中具有潜在的应用。
• Identification of differential anti-neoplastic activity of copper bis(thiosemicarbazones) that is mediated by intracellular reactive oxygen species generation and lysosomal membrane permeabilization
  作者：Christian Stefani、Zaynab Al-Eisawi、Patric J. Jansson、Danuta S. Kalinowski、Des R. Richardson

  DOI：10.1016/j.jinorgbio.2015.08.010

  日期：2015.11

  and disubstituted bis(thiosemicarbazones). This alkyl substitution pattern governed their: (1) CuII/I redox potentials; (2) ability to induce cellular 64Cu release; (3) lipophilicity; and (4) anti-proliferative activity. The potent anti-cancer Cu complex of the unsubstituted bis(thiosemicarbazone) analog, glyoxal bis(4-methyl-3-thiosemicarbazone) (GTSM), generated intracellular reactive oxygen species

  双（硫代半脲）及其铜（Cu）配合物具有独特的抗肿瘤特性。但是，它们的作用机理仍不清楚。我们检查了十二个双（硫代半氨基甲酮）的结构-活性关系，以阐明有关其抗癌功效的因素。重要的是，在配体主链的二亚胺位置上的烷基取代产生两个不同的基团，即未取代/单取代和二取代的双（硫代半咔唑酮）。这种烷基取代模式控制着它们：（1）Cu II / I氧化还原电势；（2）诱导细胞64的能力铜释放；（3）亲脂性；（4）抗增殖活性。未取代的双（硫代半碳zone酮）类似物乙二醛双（4-甲基-3-硫代半碳zone酮）（GTSM）的有效抗癌铜络合物可生成细胞内活性氧（ROS），并通过非螯合的铜螯合作用而减弱有毒的铜螯合剂四硫代钼酸盐和抗氧化剂N-乙酰-1-半胱氨酸。荧光显微镜显示，Cu（GTSM）的抗癌活性部分归因于溶酶体膜通透性（LMP）。这项研究首次凸显了ROS和LMP在双（硫代半脲酮）的抗癌活性中的作用。
• Copper complexes with dissymmetrically substituted bis(thiosemicarbazone) ligands as a basis for PET radiopharmaceuticals: control of redox potential and lipophilicity
  作者：Oliver C. Brown、Julia Baguña Torres、Katherine B. Holt、Philip J. Blower、Michael J. Went

  DOI：10.1039/c7dt02008b

  日期：——

  synthesis of a library of new dissymmetrically substituted bis(thiosemicarbazone) ligands by controlling the condensation reactions between dicarbonyl compounds and 4-substituted-3-thiosemicarbazides or using acetal protection. Copper complexes of the new ligands have been prepared by reaction with copper acetate or via transmetallation of the corresponding zinc complexes, which are convenient precursors for

  铜（II）双（thiosemicarbazone）衍生物已广泛用于正电子发射断层扫描（PET）中，以对缺氧和血流成像并用于细胞跟踪的放射性标记细胞。这些应用取决于双（硫代半脲）配合物的氧化还原电势和亲脂性的控制，可以通过改变外围配体取代基来调节。本文报道了通过控制二羰基化合物与4-取代的-3-硫代氨基脲之间的缩合反应或使用缩醛保护合成了一个新的不对称取代的双（硫代氨基脲）配体的文库。新配体的铜配合物已经通过与乙酸铜反应或通过相应的锌配合物的金属转移来制备，这些锌配合物是放射性铜配合物的快速合成的方便的前体。
• Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones
  作者：Guilin Xie、Yuhan Zhao、Changqun Cai、Guo-Jun Deng、Hang Gong

  DOI：10.1021/acs.orglett.0c03922

  日期：2021.1.15

  indole framework and/or realize indole modification. Nevertheless, the direct selective functionalization on the benzenoid core must overcome the high activity of the C-3 position and still remains highly challenging. Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually is considered as a practical

  吲哚支架是普遍存在的有用的亚结构，并且已经进行了广泛的研究以构建吲哚骨架和/或实现吲哚修饰。然而，在类苯环核上的直接选择性官能化必须克服C-3位置的高活性，并且仍然具有很高的挑战性。本文中，开发了在容易除去的导向基团存在下钯催化的吲哚的直接和特异性C-7酰化。该方法通常被认为是制备酰化吲哚的实用方法，因为在氧化条件下吲哚可以容易地转化为吲哚。尤其是，我们的策略极大地提高了二氢吲哚的烷基化收率，在先前的研究中，仅能获得令人满意的收率。此外，
• [EN] THIAZOLOPYRIMIDINONES AS MODULATORS OF NMDA RECEPTOR ACTIVITY<br/>[FR] THIAZOLOPYRIMIDINONES EN TANT QUE MODULATEURS DE L'ACTIVITÉ DU RÉCEPTEUR NMDA
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015052226A1

  公开（公告）日：2015-04-16

  The present invention relates to certain thiazolopyrimidinone compounds for use in modulating NMDA receptor activity, pharmaceutical compositions comprising such compounds and methods of treating neurological and psychiatric conditions.

  本发明涉及某些噻唑吡咯嘧啶酮化合物，用于调节NMDA受体活性，包括这些化合物的药物组合物以及治疗神经和精神疾病的方法。

表征谱图