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大蒜粉 | 2050-87-5

中文名称
大蒜粉
中文别名
二烯丙基三硫醚;大蒜素;大蒜提取物;三硫二(3-丙烯);3,3'-三硫二丙烯;蒜粉;二丙烯基三硫醚;大蒜新素;蒜;烯丙基三硫;大蒜(ALLIUMSATIVUM)鳞茎提取物;大蒜油;大蒜精;大蒜精油
英文名称
diallyl trisulfide
英文别名
DATS;diallyl trisulphide;di-2-propenyl trisulfide;allyl trisulfide;allitridin;3-(prop-2-enyltrisulfanyl)prop-1-ene
大蒜粉化学式
CAS
2050-87-5;8008-99-9
化学式
C6H10S3
mdl
MFCD00040025
分子量
178.343
InChiKey
UBAXRAHSPKWNCX-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    bp6 92°; bp0.0008 66-67°
  • 密度:
    1.085
  • 溶解度:
    可溶于丙酮、乙醇 (~3 mg/ml)、DMSO (~5 mg/ml) 和 DMF (~10 mg/ml)。
  • LogP:
    4.59
  • 物理描述:
    Liquid
  • 折光率:
    1.600-1.620
  • 碰撞截面:
    126.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
  • 保留指数:
    1283 ;1280 ;1275 ;1276 ;1282 ;1266 ;1270 ;1279 ;1292

计算性质

  • 辛醇/水分配系数(LogP):
    2.6
  • 重原子数:
    9
  • 可旋转键数:
    6
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.333
  • 拓扑面积:
    75.9
  • 氢给体数:
    0
  • 氢受体数:
    3

ADMET

毒理性
  • 在妊娠和哺乳期间的影响
大蒜(Allium sativum)含有大蒜素,通过酶大蒜酶转化为大蒜素,被认为是大蒜具有药用价值和气味的主要原因。大蒜的气味在乳汁中归因于烯丙基甲基硫化物。大蒜被用来降低胆固醇和血压。在西方国家,大蒜在哺乳期间没有特定的适应症。在印度和土耳其,大蒜被用作催乳剂,尽管没有找到关于其单独作为催乳剂的科学研究数据。催乳剂永远不能替代影响乳汁产量的可改变因素的评估和建议。大蒜作为食物和药物有着悠久的历史,并被美国食品药品监督管理局(FDA)认为是“普遍认为安全”的食品调味料,包括在哺乳期间。大蒜的气味会传递到母乳中,这可能短暂增加婴儿吸吮时间,并可能长期增强母乳喂养婴儿的食物选择。据报道,土耳其的一些母亲使用大蒜来改善她们乳汁的味道和质量。有限的科学数据发现,口服大蒜补充剂几天对哺乳母亲或婴儿没有不良影响。当作为药物使用时,大蒜在成人中通常耐受性良好,但可能会出现胃肠道副作用以及口臭和体臭。大蒜具有抗血小板作用,有出血风险的妇女应谨慎使用。大蒜可能引起过敏反应,对大蒜或其他百合科植物如风信子、郁金香、洋葱、韭菜和大葱过敏的人应避免使用。大蒜的外用可能会导致皮炎和烧伤,特别是在婴儿中应谨慎使用。一位哺乳母亲因长时间(2天)使用生碎大蒜敷料治疗自诊为念珠菌感染而严重烧伤乳房。 膳食补充剂不需要美国食品药品监督管理局的广泛市场前批准。制造商负责确保产品的安全性,但在市场营销前不需要证明膳食补充剂的安全性和有效性。膳食补充剂可能含有多种成分,标签和实际成分或其含量之间常常存在差异。制造商可以与独立组织签订合同,以验证产品或其成分的质量,但这并不证明产品的安全或有效性。由于上述问题,一个产品的临床测试结果可能不适用于其他产品。关于膳食补充剂的更详细信息可以在LactMed网站的其它地方找到。 ◉ 对哺乳婴儿的影响:母亲食用大蒜被认为会导致哺乳婴儿肠绞痛。两篇论文倾向于反驳这一说法。其中一项研究中,153位回答问卷的母亲中,那些食用了大蒜的母亲并不比那些没有食用大蒜的母亲更有可能报告她们的婴儿在过去一周内有肠绞痛。 在另一项研究中,母亲们以双盲方式每天一次服用1.5克大蒜或安慰剂胶囊,持续3天,然后询问她们在服用胶囊后婴儿是否表现出任何肠绞痛的迹象(更烦躁、哭得更多或更多气体)。在服用大蒜的20名女性中,有4人认为她们的婴儿有肠绞痛;然而,在服用安慰剂的10名女性中,有4人认为她们服用了大蒜并报告了婴儿的肠绞痛。 ◉ 对哺乳和母乳的影响:40位在分娩后第5天抱怨母乳供应不足的母亲被给予一种组合草药补充剂,即每天3次服用2粒Lactare胶囊(Pharma Private Ltd.,印度马德拉斯)。每粒胶囊含有野生芦笋200毫克,印度人参(Withania somnifera)100毫克,葫芦巴50毫克,甘草50毫克,大蒜20毫克。在治疗的第4天,没有婴儿需要补充喂养。在母亲治疗的第5天,婴儿在每次喂养前后称重,以确定摄入的牛奶量。在测试称重的当天,婴儿的牛奶摄入量平均为388毫升,液体和卡路里的摄入量被认为是足够的。由于缺乏随机化、双盲、安慰剂对照以及母乳喂养技术的母亲指导,这项研究不能被视为这些草药催乳效果的有效证据。此外,婴儿每天只哺乳6到8次,这不足以最大化乳汁供应。 在由同一研究者进行的两项研究中,给哺乳母亲服用了含有1.5克大蒜提取物的胶囊(General Nutrition Center,宾夕法尼亚州匹兹堡)。在第一项实验中,8位母亲交叉服用大蒜胶囊或安慰剂,每天一次。那些母亲服用大蒜胶囊的大蒜未接触过的婴儿在大蒜摄入后1.5到3小时期间,当乳汁中的大蒜气味最大时,与那些母亲服用安慰剂的婴儿相比,附着在乳头上的时间更长(33分钟对27分钟);然而,两组之间的总哺乳次数或总摄入量没有差异。在一项随机对照试验中,哺乳母亲在测试前3天服用大蒜胶囊或安慰剂,然后像上面的研究一样服用单粒胶囊。首次在母乳中接触大蒜的婴儿在服用大蒜后的哺乳时间比服用安慰剂后增加了30%。那些之前在母乳中接触过大蒜的婴儿在随后的大蒜接触后并没有增加哺乳时间。作者将上述研究的结果解释为对婴儿后期食物选择有积极影响(即对食物不那么“挑剔”)。
◉ Summary of Use during Lactation:Garlic (Allium sativum) contains alliin, which is metabolized by the enzyme alliinase to allicin, thought to be responsible for most of garlic's medicinal properties and odor. Garlic’s odor in milk is attributed to allyl methyl sulfide. Garlic has been used to lower cholesterol and blood pressure. It has no specific indications for use during lactation in western countries. Garlic has been used as a galactogogue in India and Turkey, although no scientific data could be located on its use alone as a galactogogue. Galactogogues should never replace evaluation and counseling on modifiable factors that affect milk production. Garlic has a long history of use as a food and medicine and is "generally recognized as safe" (GRAS) as a food flavoring by the U.S. Food and Drug Administration, including during lactation. Garlic's odor is transmitted to breastmilk, which may increase infant sucking time acutely and might enhance the breastfed infant's food choices in the long term. Some mothers in Turkey reportedly use garlic to improve the taste and quality of their milk. Limited scientific data found that a few days of oral garlic supplementation caused no adverse effects in nursing mothers or infants. When used as a medicinal, garlic is generally well tolerated in adults, but gastrointestinal side effects and bad breath and body odor may occur. Garlic has anti-platelet effects and should be used cautiously by women at risk for bleeding. Garlic can cause allergies and should be avoided by persons allergic to garlic or other members of the lily family, such as hyacinth, tulip, onion, leek, and chives. Topical application of garlic can cause dermatitis and burns and should be used with caution, especially in infants. One nursing mother received severe burns to the breast from prolonged (2 days) application of a poultice of raw, crushed garlic to treat a self-diagnosed Candida infection. Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site. ◉ Effects in Breastfed Infants:Maternal garlic ingestion has a reputation for causing colic in breastfed infants. Two papers tend to refute this claim. In one, 153 mothers who answered a questionnaire were no more likely to report colic in their infants in the previous week if they had ingested garlic than if they had not. In another study, mothers who were given either 1.5 grams of garlic or placebo capsules once daily in a blinded fashion for 3 days were asked if their infants had exhibited any signs of colic (were fussier, cried more or had more gas) after capsule ingestion. Four of 20 women who ingested garlic thought their infants had colic; however, 4 of 10 women who received placebo thought they had received garlic and reported colic in their infants. ◉ Effects on Lactation and Breastmilk:Forty women who complained of an insufficient milk supply at 5 days postpartum were given a combination herbal supplement as 2 capsules of Lactare (Pharma Private Ltd., Madras, India) 3 times daily. Each capsule contained wild asparagus 200 mg, ashwagandha (Withania somnifera) 100 mg, fenugreek 50 mg, licorice 50 mg, and garlic 20 mg. By day 4 of therapy, no infants required supplementary feeding. Infants were weighed before and after each feeding on the fifth day of maternal therapy to determine the amount of milk ingested. On the day of the test weighing, infants' milk intake averaged 388 mL, and the fluid and caloric intake was considered adequate. This study cannot be considered as valid evidence of a galactogogue effect of these herbs because it lacks randomization, blinding, a placebo control, and maternal instruction in breastfeeding technique. Additionally, infants were breastfed only 6 to 8 times daily, which is insufficient to maximize milk supply. In two studies conducted by the same investigators, capsules containing 1.5 g of garlic extract (General Nutrition Center, Pittsburgh, PA) were given to nursing mothers. In the first experiment, 8 mothers receive a garlic capsule or placebo once daily in a crossover fashion. Garlic-naive infants whose mothers ingested garlic capsules spent more time (33 vs 27 minutes) attached to the nipple during the time period of 1.5 to 3 hours after garlic ingestion when garlic odor in milk was maximal than in those whose mothers received a placebo; however, total number of nursings or total amount of milk ingestion did not differ between groups. A study randomized nursing mothers to receive garlic capsules or placebo for 3 days before testing with a single capsule as in the study above. Infants who received garlic in the milk for the first time spent 30% more time nursing than after placebo. Infants who had been previously exposed to garlic in milk, did not spend more time nursing after subsequent garlic exposure in milk. The authors interpreted the results of these studies as having a positive effect on infants' later food choices (i.e., being less "picky" about foods).
来源:Drugs and Lactation Database (LactMed)

安全信息

  • 危险等级:
    6.1(b)
  • WGK Germany:
    3
  • 海关编码:
    2930909090
  • 危险品运输编号:
    UN 2810
  • 包装等级:
    III
  • 危险类别:
    6.1(b)
  • 危险标志:
    GHS06
  • 危险性描述:
    H301
  • 危险性防范说明:
    P301 + P310

SDS

SDS:963f71f9512ba65c08b3224e591f8029
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制备方法与用途

食品添加剂最大允许使用量和残留量标准 二烯丙基三硫醚 基本信息
  • 添加剂中文名称:二烯丙基三硫醚
  • 允许使用该种添加剂的食品中文名称:食品
  • 添加剂功能:食品用香料
  • 最大允许使用量(g/kg):用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量
生物活性

Diallyl Trisulfide是从大蒜中分离出来的。这种物质能够抑制扩张性青霉 (MFC99 值: ≤ 90 μg/mL) 的生长,并通过产生活性氧 (ROS) 和破坏细胞超微结构来促进细胞凋亡,具有抗癌能力。

靶点
  • Penicillium expansum (MFC 99 值: ≤ 90)
  • Apoptosis
  • Reactive oxygen species (ROS)
化学性质
  • 黄色液体
  • 具有令人厌恶的气味
  • 沸点:112~120℃(2133Pa),或95~97℃(667Pa)或70℃(133Pa)
  • 不溶于水和乙醇,混溶于乙醚
  • 天然品存在于洋葱、大蒜等中
用途

GB 2760一2002规定为允许使用的食品用香料。

类别

可燃液体

毒性分级

高毒

急性毒性

口服 - 小鼠 LD50: 100 毫克/公斤

可燃性危险特性
  • 可燃; 火场分解有毒硫氧化物烟雾
储运特性
  • 库房低温, 通风, 干燥
  • 防火; 与氧化剂分开存放
灭火剂
  • 二氧化碳
  • 干粉
  • 砂土

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    大蒜粉L-半胱氨酸 作用下, 以 aq. phosphate buffer 为溶剂, 反应 1.83h, 生成 硫化氢
    参考文献:
    名称:
    苄基多硫化物中硫烷硫含量对硫醇触发的 H2S 释放和细胞增殖的影响。
    摘要:
    对硫化氢 (H2S) 信号通路的研究证明了过硫化物的产生和重要性,过硫化物是含有还原硫和氧化硫的活性硫物质。这些观察结果使研究人员认为氧化硫物质,包括硫烷硫 (S0),是造成许多最初归因于 H2S 的生理现象的原因。将 S0 引入生物系统的常见方法是施用有机多硫化物,例如二烯丙基三硫化物 (DATS)。然而,先前的报道表明,市售的 DATS 通常含有多硫化物的混合物,而且有机多硫化物缺乏结构-活性关系限制了我们对不同多硫化物及其在生物系统中的功能的整体理解。为了加深我们对包括 H2S 和 S0 在内的活性硫的化学生物学的兴趣,我们在这里报告了我们对一系列合成的纯苄基多硫化物(从单硫化物到四硫化物)释放 H2S 的速率和数量的研究。我们证明,H2S 仅从三硫化物和四硫化物中释放,并且这种释放需要在半胱氨酸或还原型谷胱甘肽存在下进行硫醇介导的还原。此外,我们还证明了三硫化物和四硫化物对鼠上皮 bEnd
    DOI:
    10.1016/j.freeradbiomed.2018.12.025
  • 作为产物:
    描述:
    烯丙硫醇三乙胺3,4-二氯-1,2,5-噻二唑 作用下, 以 丙醇 为溶剂, 反应 1.0h, 以74%的产率得到大蒜粉
    参考文献:
    名称:
    3,4-二氯-1,2,5-噻二唑:一种市售的亲电子硫转移剂和乙二腈的安全资源
    摘要:
    3,4-二氯-1,2,5-噻二唑是一种安全高效的硫转移试剂。通过应用这种市售试剂,通过在室温下使各种硫醇与该试剂反应,同时获得对称三硫化物和乙二腈。该试剂无毒、价格低廉且可商购。此外,在反应完成后,在所有情况下都没有检测到更高阶的多硫化物。反应时间短(20-50 分钟)、优异的选择性和三硫化物的高产率是该试剂制备三硫化物的一些吸引人的优点。该反应是一锅法,不需要中间体的分离纯化。该过程很容易扩大到 5 克。提出了一种解释化学的机制。
    DOI:
    10.1080/17415993.2021.1991928
  • 作为试剂:
    描述:
    3,3,3-膦三基三丙酸大蒜粉重水 作用下, 以 氘代乙腈 为溶剂, 生成 tris(2-carboxyethyl)phosphine oxide 、 tris(2-carboxyethyl)phosphine-sulfide
    参考文献:
    名称:
    Trisulfide Modification Impacts the Reduction Step in Antibody–Drug Conjugation Process
    摘要:
    Antibody-drug conjugates (ADCs) utilizing cysteine-directed linker chemistry have cytotoxic drugs covalently bound to native heavy heavy and heavy light interchain disulfide bonds. The manufacture of these ADCs involves a reduction step followed by a conjugation step. When tris(2-carboxyethyl)phosphine (TCEP) is used as the reductant, the reaction stoichiometry predicts that for each molecule of TCEP added, one interchain disulfide should be reduced, generating two free thiols for drug linkage. In practice, the amount of TCEP required to achieve the desired drug-to-antibody ratio often exceeds the predicted, and is variable for different lots of monoclonal antibody starting material. We have identified the cause of this variability to be inconsistent levels of interchain trisulfide bonds in the monoclonal antibody. We propose that TCEP reacts with each trisulfide bond to form a thiophosphine and a disulfide bond, yielding no net antibody free thiols for conjugation. Antibodies with higher levels of trisulfide bonds require a greater TCEP:antibody molar ratio to achieve the targeted drug-to-antibody ratio.
    DOI:
    10.1021/bc4000299
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文献信息

  • Trisulfides over disulfides: highly selective synthetic strategies, anti-proliferative activities and sustained H<sub>2</sub>S release profiles
    作者:Debojit Bhattacherjee、Abu Sufian、Sulendar K. Mahato、Samiyara Begum、Kaustav Banerjee、Sharmistha De、Hemant Kumar Srivastava、Krishna P. Bhabak
    DOI:10.1039/c9cc05562b
    日期:——
    Temperature- and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.
    证明了温度和溶剂诱导的三硫化物和二硫化物的选择性合成。使用Na 2 S作为硫转移剂,可在温和,绿色,无催化剂和无添加剂的条件下实现显着的选择性。这项研究表明,对于持续释放H 2 S和有效的抗癌活性,三硫化物通常比二硫化物更好。
  • The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: structural, mechanistic, and synthetic studies
    作者:Eric. Block、Saleem. Ahmad、James L. Catalfamo、Mahendra K. Jain、Rafael. Apitz-Castro
    DOI:10.1021/ja00282a033
    日期:1986.10
    Synthese de l'ajoene (oxyde-9 de trithia-4,5,9 dodecatriene-1,6,11) et de quelques analogues
    合成 de l'ajoene (oxyde-9 de trithia-4,5,9 dodecatriene-1,6,11) et de quelques 类似物
  • Methods of Treating Ocular Diseases Using Derivatives of Lipoic Acid
    申请人:Encore Health, LLC
    公开号:US20150246903A9
    公开(公告)日:2015-09-03
    Dithiol compounds and derivatives thereof are disclosed. The agents are useful for treating ocular disease, especially presbyopia and cataract.
    公开了二硫化合物及其衍生物。这些药物对治疗眼部疾病,特别是老视和白内障,具有益处。
  • Controllable thioester-based hydrogen sulfide slow-releasing donors as cardioprotective agents
    作者:Hong Yao、Shanshan Luo、Junkai Liu、Shaowen Xie、Yanpeng Liu、Jinyi Xu、Zheying Zhu、Shengtao Xu
    DOI:10.1039/c9cc02829c
    日期:——
    membrane potential (MMP) loss and lactate dehydrogenase (LDH) release in H2O2-stimulated H9c2 cells. More importantly, donor 5e exhibited a potent cardioprotective effect in an in vivo myocardial infarction (MI) mouse model by reducing myocardial infarct size and cardiomyocyte apoptosis. Taken together, our studies demonstrated that these new allyl thioesters are potential cardioprotective agents by releasing
    硫化氢(H 2 S)是重要的信号分子,在许多生理和病理过程中均具有有希望的保护作用。然而,由于缺乏合适的H 2 S供体来模拟其在体内的缓慢释放过程,因此阻碍了对H 2 S的研究。在这里,我们报告了一系列基于硫酯的H 2 S供体的合理设计,合成和生物学评估。这些半胱氨酸激活的H 2 S供体释放H 2S以缓慢且可控的方式。包含烯丙基部分的大多数供体在氧化损伤的H9c2细胞模型中显示出显着的细胞保护作用。在H 2 O 2刺激的H9c2细胞中,最有效的供体5e减少了线粒体膜电位(MMP)的损失和乳酸脱氢酶(LDH)的释放。更重要的是,供体5e通过减少心肌梗死面积和心肌细胞凋亡,在体内心肌梗死(MI)小鼠模型中表现出了强大的心脏保护作用。两者合计,我们的研究表明,这些新的烯丙基硫酯通过释放H 2 S是潜在的心脏保护剂。
  • Selectivity of diallyl trisulfides (DATS) in reducing HAuCl4 to produce gold nanoparticles: a detailed investigation
    作者:NILADRI SEKHAR MANDAL、ARUNAVO CHATTERJEE、PRADIPTA PURKAYASTHA
    DOI:10.1007/s12039-021-01967-6
    日期:2021.9
    capping as well as reducing agent to synthesize gold nanoparticles (TS-GNPs). In the process, it was discovered that among the selected DATs, only 1,3-di(but-1-ene)trisulfane could serve the purpose because of structural reasons. The reason for this intriguing selectivity has been investigated in detail using the experimental findings and theoretical calculations of the frontier molecular orbitals
    球根大蒜(Allium sativum) 具有强烈的味道和刺鼻的气味,广泛用于烹饪制剂和民间药物。使用这种成分合成的银和金纳米粒子 (NPs) 也显示出药用和治疗效力。大蒜含有有机硫化合物,如二烯丙基硫化物 (DAS)、二烯丙基二硫化物 (DADS) 和二烯丙基三硫化物 (DATS)。这些化合物作为抗癌药物具有至关重要的意义。这里报道的是一系列具有不同取代基的 DATS 的合成,并且可能作为封端剂和还原剂来合成金纳米粒子 (TS-GNP)。在此过程中,发现在选定的 DAT 中,由于结构原因,只有 1,3-二(丁-1-烯)三硫烷可以达到目的。 图形摘要 据报道,合成了一系列具有药用意义的对称有机三硫化物作为二烯丙基三硫化物 (DATS) 的结构类似物,以尝试构建有机硫化合物诱导的金纳米粒子 (GNP)。该批次中只有 1,3-Di(but-1-ene)trisulfane 能够还原氯金酸以合成受保护的
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

香菇素 甲基烯丙基三硫醚 甲基乙基三硫醚 甲基丙基三硫醚 甲基(1-甲基乙基)三硫醚 大蒜粉 双十二烷基三硫醚 二甲基三硫 二甲基-d6三硫醚 二异丙基三硫醚 二叔十二烷基三硫化物 二乙基三硫醚 二丙基三硫醚 二-叔-丁基三硫化物 二(异丙氧基硫代羰基)三硫醚 二(二甲硫基氨基甲酰)三硫醚 二(乙氧基硫代羰基)三硫醚 二(三氯甲基)三硫醚 二(3-羟基丙基)三硫醚 二(2-羟基乙基)三硫醚 二(2-氯乙基)三硫醚 乙基丙基三硫醚 丙基烯丙基三硫醚 三氟-(三氟甲基硫基二硫基)甲烷 N(1),N(3)-二甲基-1,3-三硫烷二硫代甲酰胺 6-肼基-N,N-二(丙-2-烯-1-基)哒嗪-3-胺二盐酸 3,3'-三硫代二丙酰胺 1,1'-三硫代二[N,N-二丁基-硫代甲酰胺] 2-<(1-methyl-2-oxopropyl)trithio>-3-pentanone 3-<(1-methyl-2-oxopropyl)trithio>-2-pentanone 3-<(1-methyl-2-oxobutyl)trithio>-2-pentanone diethyl 4,4'-trithiobis(butanesulfinate) 7-methyl-4,5,6,9,10-pentathiatrideca-1,12-diene 8-methyl-4,5,6,9,10-pentathiatrideca-1,12-diene bis(1-ethyl-2-oxopropyl) trisulfide 1,4,5,6-Oxatrithiocane 2-(2,3,3,4,5,5-Hexamethylhexan-2-yltrisulfanyl)-2,3,3,4,5,5-hexamethylhexane Di-tert-nonyl polysulfide 3,3'-(Ethane-1,2-diyl)bis(N,N-dimethyltrisulfane-1-carbothioamide) O-Ethyl tert-butyltrisulfane-1-carbothioate O-Ethyl butyltrisulfane-1-carbothioate N(1),N(3)-Dibutyl-1,3-trisulfanedicarbothioamide 1,3-Trisulfanedicarbothioamide, N,N'-dicyclohexyl- 1,1'-Trithiobis(N,N-dicyclohexylmethanethioamide di-tert-pentyl trisulfide Dipentylxanthogentrisulfid 4,4,7,7-tetramethyl-1,2,3,5,6-pentathiepane 1-Butanesulfinic acid, 4,4'-trithiobis-, disodium salt 1,2,3,5,6-Pentathiepane, 4,7-dimethyl- Methyl tert-butyltrisulfane-1-carboxylate

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