摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

1,3-二羟甲基-5,5-二甲基海因 | 6440-58-0

中文名称
1,3-二羟甲基-5,5-二甲基海因
中文别名
1,3-二羟甲基-5,5-二甲基乙内酰脲;DMDM乙内酰脲;1,3-二(羟甲基)-5,5-二甲基咪唑烷-2,4-二酮;DMDM 乙内酰脲;二羟甲基海因
英文名称
1,3-bis-hydroxymethyl-5,5-dimethyl-imidazolidine-2,4-dione
英文别名
1,3-dimethylol-5,5-dimethylhydantoin;DMDM Hydantoin;1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
1,3-二羟甲基-5,5-二甲基海因化学式
CAS
6440-58-0
化学式
C7H12N2O4
mdl
MFCD00467199
分子量
188.183
InChiKey
WSDISUOETYTPRL-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

  • 熔点:
    1.00-2.5 °C
  • 沸点:
    303.7±52.0 °C(Predicted)
  • 密度:
    1.349±0.06 g/cm3(Predicted)
  • 溶解度:
    DMSO(少量)、甲醇(少量)
  • LogP:
    -2.9 at 20℃
  • 物理描述:
    Liquid
  • 颜色/状态:
    Solid
  • 气味:
    Odorless
  • 蒸汽压力:
    9.0X10-8 mm Hg at 25 °C
  • 表面张力:
    72.4 mN/m at 20 °C /0.998 g/L solution/
  • 解离常数:
    pKa1 = 13.43, pKa2 = 13.41 (est)

计算性质

  • 辛醇/水分配系数(LogP):
    -0.2
  • 重原子数:
    13
  • 可旋转键数:
    2
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.714
  • 拓扑面积:
    81.1
  • 氢给体数:
    2
  • 氢受体数:
    4

ADMET

代谢
甲醛可能通过吸入、口服或皮肤接触被吸收。它是所有细胞中的基本代谢中间体,在丝氨酸、甘酸、甲酸和胆碱的正常代谢过程中产生,也通过N-、S-和O-甲基化合物的脱甲基作用产生。外源性甲醛通过酶甲醛脱氢酶在初始接触点被代谢成甲酸盐。甲醛氧化成甲酸盐后,碳原子进一步氧化成二氧化碳,或者通过四氢叶酸依赖的一碳生物合成途径并入嘌呤、胸腺嘧啶氨基酸中。甲醛不会在体内储存,而是通过尿液(主要作为甲酸)排出,或并入其他细胞分子中,或作为二氧化碳呼出。
Formaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (L962)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
识别和使用:DMDM乙内酰是一种化妆品防腐剂。它被描述为一种广谱抗菌剂,对真菌、酵母菌以及革兰氏阳性菌和革兰氏阴性菌都有效。人类暴露和毒性:DMDM乙内酰是一种释放甲醛的物质,这意味着该物质可以释放甲醛甲醛被分类为致癌物和致敏物。进行了一项为期一年的研究,以检查对13种常见防腐剂的过敏反应频率。在这项研究中,对2295名连续的疑似过敏性接触性皮炎门诊患者进行了测试。研究的防腐剂阳性反应率如下:甲醛5.7%,DMDM乙内酰1.7%。DMDH乙内酰还会导致不可逆转的眼睛损伤。动物研究:通过兔子的皮肤研究发现,实验物质对接受0.008 g/kg剂量的兔子的皮肤实际上无刺激性,对接受0.8 g/kg剂量的兔子有轻度到中度刺激性。在一项发育研究中,通过灌胃方式给兔子口服了含有55% DMDM乙内酰的溶液。仅报告了一起与测试物质相关的死亡。对照组(阳性和阴性)与实验组在尸检发现的发生率上没有显著差异。阴性对照组和实验组在外观和骨骼胎儿检查结果上也没有显著差异。在给大鼠口服后,测试物质没有在大鼠睾丸DNA中诱导链断裂或交联。在Salmonella/mammalian-microsome预培养致突变性试验中测试了含有55% DMDM乙内酰的溶液,使用了以下S. typhimurium菌株,并进行了代谢激活:TA-98、TA-100、TA-1535、TA-1537和TA-1538。在未进行代谢激活的情况下,TA-98菌株出现了阳性反应(平均回复体数量增加了3.2倍);在代谢激活后,增加了1.9倍。此外,TA-100菌株在代谢激活和未激活的情况下分别增加了2.2倍和1.7倍。在L5178Y TK+/-小鼠淋巴瘤试验中测试了含有55% DMDM乙内酰的溶液,并进行了代谢激活。在测试条件下,测试物质在存在和不存在代谢激活的情况下,都显著增加了处理培养物的突变频率。
IDENTIFICATION AND USE: DMDM hydantoin is a cosmetic preservative. It is described as being a broad-spectrum antimicrobial agent, effective against fungi, yeast, and gram-positive and gram-negative bacteria. HUMAN EXPOSURE AND TOXICITY: DMDM Hydantoin is a formaldehyde releaser, which means that the substance can release a formaldehyde. Formaldehyde is classified as carcinogenic and allergenic. A 1-year study was conducted to examine the frequency of sensitization to a series of 13 common preservatives. A group of 2,295 consecutive outpatients with suspected allergic contact dermatitis was tested in this study. The rates of positive reactions to the preservatives studied are as follows: formaldehyde 5.7%, and DMDM hydantoin 1.7%. DMDH hydantoin also causes irreversible eye damage. ANIMAL STUDIES: From the dermal study in rabbits it was concluded that the test material was practically nonirritating to the skins of rabbits receiving the 0.008 g/kg dose and mildly to moderately irritating to those receiving the 0.8 g/kg dose. In a developmental study a 55% DMDM Hydantoin solution was administered orally via gavage to rabbits. Only one test substance-related death was reported. There were no significant differences between control (positive and negative) and experimental groups concerning the incidence of necropsy findings. The results of external and skeletal fetal examinations were not significantly different between negative control and experimental groups. The test substance did not induce strand breaks or cross-links in rat testicular DNA after oral administration to rats. A 55% DMDM Hydantoin solution was tested in the Salmonella/mammalian-microsome preincubation mutagenicity assay using the following strains of S. typhimurium with and without metabolic activation: TA-98, TA-100, TA-1535, TA-1537, and TA-1538. A positive response (3.2 fold increase in average number of revertants) was noted for strain TA-98, without metabolic activation; with metabolic activation, a 1.9-fold increase was noted. Additionally, increases of 2.2-fold and 1.7-fold were noted for strain TA-100 with and without activation, respectively. A 55% DMDM Hydantoin solution was tested in the L5178Y TK+/- mouse lymphoma assay, with and without metabolic activation. Under the conditions of testing, the test substance caused a significant dose-dependent increase in the mutant frequency of cultures treated in both the presence and absence of metabolic activation.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
DMDM乙内酰是一种释放甲醛的化合物。当细胞内甲醛平饱和了甲醛脱氢酶的活性时,可能会发生甲醛中毒,使得未经代谢的完整分子发挥作用。甲醛已知能够在蛋白质和DNA之间形成交联,并代谢整合进入大分子(DNA、RNA和蛋白质)中。
DMDM hydantoin is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (L962, L1896)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌物分类
对人类致癌(针对甲醛)。
1, carcinogenic to humans (for formaldehyde). (L135)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 健康影响
DMDM乙内酰释放甲醛,这是一种已知的人类致癌物。
DMDM hydantoin releases formaldehyde, a known human carcinogen. (L962, L1896)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 暴露途径
口服(L962);吸入(L962);皮肤给药(L962)
Oral (L962) ; inhalation (L962) ; dermal (L962)
来源:Toxin and Toxin Target Database (T3DB)
吸收、分配和排泄
0.1毫升的溶液中含有0.1毫居里的1,3-二羟甲基-5,5'-二甲基海因-5-(14)-C被应用于年轻的成年雄性Sprague-Dawley大鼠的中背部区域。72小时后,超过90%的施用剂量被回收;回收到的活性中有超过98%局限于给药部位。在处死时,不到1%的放射性分布在所有身体组织中。报告称,胃肠道、肝脏和骨髓的放射性计数较高。对于大多数组织样本,没有证据表明DMDM海因或其代谢物有积累。DMDM海因及其代谢物主要通过尿液排出。在72小时期间,尿液中(14)C活性的量减少了大约6倍;粪便中的放射性活动保持大约恒定,且显著低于尿液。
A 0.1 mL aqueous solution containing 0.1 mCi of 1,3-dihydroxymethyl-5,5'-dimethylhydantoin-5-(14)-C was applied to the middorsal area of young adult male Sprague-Dawley rats. After 72 hours, more than 90% of the applied dose was recovered; more than 98% of the recovered activity was confined to the dose site. At the time of killing, less than 1% of the radioactivity was distributed in all body tissues. The higher counts of radioactivity were reported for the gastrointestinal tract, liver, and bone marrow. For most tissue samples, there was no evidence of accumulation of DMDM Hydantoin or its metabolites. DMDM Hydantoin and its metabolites are excreted primarily via the urine. The amount of (14)C activity in the urine decreased approximately 6 times over a 72-hour period; radioactivity in the feces remained approximately constant and significantly below that of the urine.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险品标志:
    Xi
  • 安全说明:
    S26,S36/37
  • 危险类别码:
    R22,R36,R43
  • 海关编码:
    2933990090
  • 危险性防范说明:
    P261,P305+P351+P338
  • 危险性描述:
    H302,H315,H319,H335

制备方法与用途

理化性质

无色透明液体,略带醛味。在环境温度低于15℃时会析出结晶,并且是一种甲醛释放物。它能溶于和醇,耐热性较好。

用途

DMDM乙内酰又名1,3-二羟甲基-5,5-二甲基海因(英文缩写为DMDMH),是一种广谱、高效的抗菌防腐剂。通过释放甲醛来抑制革兰氏阳性菌和阴性菌、霉菌及酵母菌等,并且与各种乳化剂、表面活性剂配伍性良好。

耐用且可再生的抗菌织物是通过采用前体杀生物剂二羟甲基二甲基乙内酰DMDMH)的创新化学技术在化学整理过程中制备的。

使用范围

这种防腐剂在较宽的pH值和温度范围内都保持稳定,不受阴、阳离子及非离子型表面活性剂的影响。建议在pH=3~10及小于60℃的条件下使用,作用温和,安全无毒且对皮肤和眼粘膜均无刺激。

DMDMH的应用范围很广,包括工业产品如液体洗涤剂、基表面活性剂、软皂、基涂料、织物柔软剂、室内除臭剂、空气清新剂、聚合物乳液、织物保护涂层、建筑涂料、基凝胶、密封胶和嵌缝胶、纸张乳液涂层、基油墨、木材防腐剂等。此外,它还可以应用于个人护理产品如各种中高档护肤化妆品、膏霜、湿毛巾、香波、啫喱、沐浴露、洗涤剂等日用化学品的防腐,用量通常为0.1%~0.6%。

为了达到最佳的防腐防霉效果,DMDMH常与防霉剂配合使用。其独特的罐内空间保护性能使其具有特殊的应用价值,溶性产品可以直接加入。

制备

一种防冻型DMDM乙内酰的制备方法如下:

  1. 给2L三口圆底烧瓶装配有搅拌器和温度调节器。
  2. 将600g甲醛置入烧瓶中,用氢氧化钠溶液将pH调节至7.4。
  3. 加入500g的海因,观察到剧烈放热并出现温度上升,大部分海因溶解。
  4. 氢氧化钠溶液将pH调节至8.3,继续在55℃下搅拌反应混合物1小时。
  5. 加入175g的,然后冷却至室温。
  6. 加入10.5g NH₄Cl,搅拌均匀。
  7. 最后将pH调节至7.0。

上述产物即为防冻型DMDM乙内酰

应用

DMDMH是一种广谱抗菌剂,对革兰氏阳性菌和阴性菌有很好的抑制杀灭作用,并且对酵母菌及霉菌有一定的抑制作用。广泛应用于香波、调理剂、膏霜、沐浴液等液状化妆品中,在洗去型和驻留型产品中的应用也十分安全有效。

DMDMH主要用于洗发香波、护发素、化妆品作杀菌防腐剂

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
  • 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:
    参考文献:
    名称:
    Low free formaldehyde methylolhydantoin compositions
    摘要:
    提供含有低于总组成重量0.1%的游离甲醛的二甲基双(5-羟甲基异噶唑)酮、单甲基双(5-羟甲基异噶唑)酮和二甲基异噶唑的组合物,其中二甲基双(5-羟甲基异噶唑)酮与单甲基双(5-羟甲基异噶唑)酮的重量比范围为约1:1.25至约3.5:1。这些组合物可以通过以下方法制备:(1)反应二甲基异噶唑和含甲醛源,其中甲醛与二甲基异噶唑的摩尔比范围为约1.2:1至约1.55:1;或(2)混合(a)含有大于约0.1%游离甲醛的甲醛双(5-羟甲基异噶唑)酮的水溶液,重量占80%至90%,与(b)占100%水溶液和二甲基异噶唑总重量的20%至10%的二甲基异噶唑。
    公开号:
    US05405862A1
  • 作为产物:
    描述:
    聚合甲醛5,5-二甲基海因 、 sodium hydroxide 作用下, 反应 2.17h, 以95.6%的产率得到1,3-二羟甲基-5,5-二甲基海因
    参考文献:
    名称:
    一种1,3-二羟甲基-5,5-二甲基乙内酰脲的制备方法
    摘要:
    本发明属于精细化工技术领域,具体涉及一种1,3‑二羟甲基‑5,5‑二甲基乙内酰脲的制备方法,以多聚甲醛和5,5‑二甲基乙内酰脲为原料,水为溶剂,碱性催化剂作用下,通过羟甲基化反应,制备1,3‑二羟甲基‑5,5‑二甲基乙内酰脲。本发明提出了一种新的合成工艺,甲醛为有毒刺激性物质,该工艺避免了使用甲醛溶液,有效改善生产车间环境,提高生产安全性,且无三废排放,为绿色合成工艺。
    公开号:
    CN114014811A
点击查看最新优质反应信息

文献信息

  • [EN] IMPROVED CORROSION AND MICROBIAL CONTROL IN HYDROCARBONACEOUS COMPOSITIONS<br/>[FR] LUTTE AMÉLIORÉE CONTRE LA CORROSION ET CONTRE LES MICROBES DANS DES COMPOSITIONS HYDROCARBONÉES
    申请人:ANGUS CHEMICAL
    公开号:WO2009140062A1
    公开(公告)日:2009-11-19
    Provided are additives of formula I for use in hydrocarbonaceous compositions, such as petroleum or liquid fuels: (I) wherein R1, R2, R3, R4, and R5 are as defined herein. The additives improve the corrosion resistance of the compositions. The additives also enhance the antimicrobial efficacy of any added biocides contained in such compositions.
    提供了用于石油或液体燃料等碳氢化合物组合物中的化学添加剂的化学式I:(I)其中R1、R2、R3、R4和R5如本文所定义。这些添加剂提高了组合物的耐腐蚀性能。这些添加剂还增强了这些组合物中任何添加的生物杀菌剂的抗菌效果。
  • COMBINATIONS OF ALKYLAMIDOTHIAZOLES AND PRESERVATIVES
    申请人:BEIERSDORF AG
    公开号:US20160015615A1
    公开(公告)日:2016-01-21
    Disclosed are active ingredient combinations of alkylamidothiazoles and one or more cosmetically or dermatologically acceptable preservatives.
    揭示了烷基噻唑和一种或多种在化妆品或皮肤科学上可接受的防腐剂的活性成分组合。
  • COMPOUNDS FOR PREVENTING, REDUCING AND/OR ALLEVIATING ITCHY SKIN CONDITION(S)
    申请人:SCHMAUS Gerhard
    公开号:US20160008297A1
    公开(公告)日:2016-01-14
    The present invention primarily relates to the use of one or more specific compounds and/or one or more respective salt(s) thereof for preventing, reducing or alleviating itchy skin condition(s), and/or as PAR-2 antagonist. Furthermore, the present invention relates to compositions (products or, respectively, formulations), in particular for topical administration, preferably cosmetic or pharmaceutical compositions, in particular for preventing, reducing or alleviating one or more itchy skin conditions and/or for providing a PAR-2 antagonistic effect, comprising or consisting of an effect amount of such compound(s) and/or salt(s) and one or more cosmetically and/or pharmaceutically acceptable carriers.
    本发明主要涉及使用一种或多种特定化合物和/或其一个或多个相应盐来预防、减少或缓解瘙痒皮肤状况,和/或作为PAR-2拮抗剂。此外,本发明涉及组合物(产品或相应的配方),特别是用于局部给药,优选为化妆品或药用组合物,特别是用于预防、减少或缓解一种或多种瘙痒皮肤状况和/或产生PAR-2拮抗作用的组合物,包括或由效果量的这种化合物和/或盐以及一个或多个化妆品和/或药用可接受载体组成。
  • Compositions Containing Diethanol Amine Esterquats
    申请人:Loeffler Matthias
    公开号:US20110237667A1
    公开(公告)日:2011-09-29
    The invention relates to compositions containing one or more compounds of the formula (1), wherein R 1 CO and R 2 CO are linear or branched saturated acyl groups independent of each other, having 18 to 24 C atoms, and A − is a counter-ion, and the total amount of C 18-23 -alkyl COO groups is 40.0 wt.-% or more, based on all groups R 1 COO— and R 2 COO—. The compositions are, for example, cosmetic, dermatological, or pharmaceutical compositions.
    该发明涉及含有一个或多个式(1)化合物的组合物,其中R1CO和R2CO是线性或支链饱和脂肪酰基,独立于彼此,具有18至24个碳原子,A-是一个对离子,C18-23-烷基COO基团的总量为40.0重量%或更多,基于所有基团R1COO-和R2COO-。这些组合物例如是化妆品、皮肤科或药用组合物。
  • COSMETIC COMPOSITION
    申请人:Knappe Thorsten
    公开号:US20100028272A1
    公开(公告)日:2010-02-04
    A cosmetic agent, in particular a styling agent, containing, in a cosmetically acceptable carrier, a) at least one copolymer A made of at least one monomer A1 selected from acrylic acid, methacrylic acid, acrylic acid alkyl esters, and methacrylic acid alkyl esters, and at least one amphoteric monomer A2 selected from (meth)acryloylalkylbetaines of formula (A2-I) and (meth)acryloylalkylamine oxides of formula (A2-II), such that in formula (A2-I) and in formula (A2-II), R 1 denotes H or CH 3 , R 2 and R 3 , mutually independently in each case, denote optionally branched C 1-10 alkyl, and n denotes an integer from 1 to 20, and b) at least one film-forming and/or setting amphoteric polymer B different from copolymer A; and use of the agents for the temporary deformation of hairs.
    一种化妆品剂,特别是一种造型剂,包含在一种在化妆上可接受的载体中,a) 至少一种由至少一种从丙烯酸甲基丙烯酸丙烯酸烷基酯和甲基丙烯酸烷基酯中选择的单体A1制成的共聚物A,以及至少一种从式(A2-I)的(甲基)丙烯酰烷基甜菜碱和式(A2-II)的(甲基)丙烯酰烷基胺氧中选择的两性单体A2,使得在式(A2-I)和式(A2-II)中,R1代表H或CH3,R2和R3,在每种情况下相互独立地表示可选的支链C1-10烷基,n代表1到20之间的整数,以及b) 至少一种与共聚物A不同的成膜和/或固定两性聚合物B;以及使用这些剂对头发进行暂时变形。
查看更多

同类化合物

(R)-4-异丙基-2-恶唑烷硫酮 麻黄恶碱 顺-八氢-2H-苯并咪唑-2-酮 顺-1-(4-氟苯基)-4-[1-(4-氟苯基)-4-羰基-1,3,8-三氮杂螺[4.5]癸-8-基]环己甲腈 非达司他 降冰片烯缩醛3-((1S,2S,4S)-双环[2.2.1]庚-5-烯-2-羰基)恶唑烷-2-酮 阿齐利特 阿那昔酮 阿洛双酮 阿帕鲁胺 阿帕他胺杂质2 铟烷-2-YL-甲基胺盐酸 钾3-{2-[3-氰基-3-(十二烷基磺酰基)-2-丙烯-1-亚基]-1,3-噻唑烷-3-基}-1-丙烷磺酸酯 钠2-{[4,5-二羟基-3-(羟基甲基)-2-氧代-1-咪唑烷基]甲氧基}乙烷磺酸酯 重氮烷基脲 詹氏催化剂 解草恶唑 解草噁唑 表告依春 螺莫司汀 螺立林 螺海因氮丙啶 螺[咪唑烷-4,3'-吲哚啉]-2,2',5-三酮 螺[1-氮杂双环[2.2.2]辛烷-8,5'-咪唑烷]-2',4'-二酮 苯甲酸,4-氟-,2-[5,7-二(三氟甲基)-1,8-二氮杂萘-2-基]-2-甲基酰肼 苯氰二硫酸,1-氰基-1-甲基-4-氧代-4-(2-硫代-3-噻唑烷基)丁酯 苯妥英钠杂质8 苯妥英钠 苯妥英-D10 苯妥英 苯基硫代海因半胱氨酸钠盐 苯基硫代乙内酰脲-谷氨酸 苯基硫代乙内酰脲-蛋氨酸 苯基硫代乙内酰脲-苯丙氨酸 苯基硫代乙内酰脲-色氨酸 苯基硫代乙内酰脲-脯氨酸 苯基硫代乙内酰脲-缬氨酸 苯基硫代乙内酰脲-异亮氨酸 苯基硫代乙内酰脲-天冬氨酸 苯基硫代乙内酰脲-亮氨酸 苯基硫代乙内酰脲-丙氨酸 苯基硫代乙内酰脲-D-苏氨酸 苯基硫代乙内酰脲-(NΕ-苯基硫代氨基甲酰)-赖氨酸 苯基乙内酰脲-甘氨酸 苏氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1) 色氨酸标准品002 膦酸,(2-羰基-1-咪唑烷基)-,二(1-甲基乙基)酯 脱氢-1,3-二甲基尿囊素 脱氢-1,3,8-三甲基尿囊素 聚(d(A-T)铯)