(E)-rac-1,7,7-trimethyl-3-(4-methyl-benzylidene)-bicyclo[2.2.1]heptan-2-one | 1782069-81-1

• 物质功能分类: 分析化学 - 标准品 - 分析标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-rac-1,7,7-trimethyl-3-(4-methyl-benzylidene)-bicyclo[2.2.1]heptan-2-one
• 英文别名: 3-(4-methylbenzylidene)-camphor；4-methylbenzylidenecamphor；p-methylbenzylidene-camphor；3-(4-methylbenzylidene)-dl-camphor；(+/-)-1,7,7-trimethyl-3-[(4-methylphenyl)methylene]bicyclo[2.2.1]heptan-2-one；Enzacamene；(3E)-1,7,7-trimethyl-3-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-2-one
• CAS: 1782069-81-1；36861-47-9
• 化学式: C₁₈H₂₂O
• 分子量: 254.372
• InChiKey: HEOCBCNFKCOKBX-SDNWHVSQSA-N

物化性质

• 熔点：
  66-68°C
• 沸点：
  198-200 °C
• 密度：
  1.064±0.06 g/cm3(Predicted)
• 溶解度：
  不溶于水； DMSO 中≥10 mg/mL；乙醇中≥111.2 mg/mL
• LogP：
  3.385 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

基于大鼠药代动力学研究的发现，建议口服给药后吸收的恩扎卡米尼经过广泛的首过肝脏代谢。在大鼠口服恩扎卡米尼（4-MBC）后，血浆和尿液中检测到的代谢物为3-(4-羧基苄基亚肼)樟脑和四种3-(4-羧基苄基亚肼)羟基樟脑的同分异构体，其中羟基位于樟脑环系统中的3-(4-羧基苄基亚肼)-6-羟基樟脑为主要代谢物。然而，在达到峰值浓度后，3-(4-羧基苄基亚肼)-6-羟基樟脑的血液浓度低于检测限。通过细胞色素P450系统介导的羟基化反应，形成3-(4-羟甲基苄基亚肼)樟脑。这个代谢物通过醇脱氢酶和醛脱氢酶的氧化作用进一步氧化为3-(4-羧基苄基亚肼)樟脑，并且可能通过CYP450系统进一步羟基化为3-(4-羧基苄基亚肼)-6-羟基樟脑。

Based on the findings of a rat pharmacokinetic study, it is proposed that absorbed enzacamene following oral administration undergo extensive first-pass hepatic metabolism. Following oral administration of enzacamene (4-MBC) in rats, detected metabolites in the plasma and urine were 3-(4-carboxybenzylidene)camphor and as four isomers of 3-(4-carboxybenzylidene)hydroxycamphor containing the hydroxyl group located in the camphor ring system with 3-(4-carboxybenzylidene)-6-hydroxycamphor as the major metabolite. However the blood concentrations of 3-(4-carboxybenzylidene)-6-hydroxycamphor were below the limit of detection following peak concentration. Via hydroxylation mediated by cytochrome P450 system, 3-(4-hydroxymethylbenzylidene)camphor is formed. This metabolite is further oxidized to 3-(4-carboxybenzylidene)camphor via oxidation of alcohol dehydrogenase and aldehyde dehydrogenase, and may be further hydroxylated to form 3-(4-carboxybenzylidene)-6-hydroxycamphor mediated by CYP450 system.

来源:DrugBank

毒理性

• 蛋白质结合

无药代动力学数据可用。

No pharmacokinetic data available.

来源:DrugBank

吸收、分配和排泄

• 吸收

防晒霜配方中恩扎卡米浓度为10%（重量/重量）的恩扎卡米在健康女性志愿者全身涂抹2mg/cm^2，连续使用四天后，其最大血浆浓度为16ng/mL。口服恩扎卡米后，恩扎卡米（4-MBC）及其主要代谢物3-（4-羧基苄基亚胺）樟脑的血药浓度在10小时内达到峰值。

The maximum plasma concentration of enzacamene was 16ng/mL in healthy female volunteers following daily whole-body topical application of 2mg/cm^2 of sunscreen formulation at 10% (weight/weight) for four days. Blood concentration of enzacamene (4-MBC) and its main metabolite, 3-(4-carboxybenzylidene)camphor, peaked within 10 h after oral administration of enzacamene.

来源:DrugBank

吸收、分配和排泄

• 消除途径

在女性和男性志愿者中观察到的尿液中恩扎卡米浓度分别为4 ng/mL和4 ng/mL。在大鼠药代动力学研究中，口服给药的大部分恩扎卡米以3-(4-羧基苄基)莰和较小程度的3-(4-羧基苄基)-6-羟基莰形式在粪便中回收。两种代谢物的葡萄糖苷酸也可在粪便中检测到。在尿液中，3-(4-羧基苄基)羟基莰的一个对映异构体[3-(4-羧基苄基)-6-羟基莰]是主要的代谢物，其他对映异构体和3-(4-羧基苄基)莰仅是随尿液排出的少量代谢物。来自两种主要4-MBC代谢物的葡萄糖苷酸的肠肝循环可能解释了4-MBC代谢物随尿液缓慢排泄和尿液中回收的给药剂量比例较小的情况。

The urine concentration of 4 ng/mL and 4 ng/mL of enzacamene were observed in female and male volunteers, respectively. In a rat pharmacokinetic study, most of orally administered enzacamene was recovered in in feces as 3-(4-carboxybenzylidene)camphor and, to a smaller extent, as 3-(4-carboxybenzylidene)-6-hydroxycamphor. Glucuronides of both metabolites were also detectable in faces. In urine, one isomer of 3-(4-carboxybenzylidene)hydroxycamphor was the predominant metabolite [3-(4-carboxybenzylidene)-6-hydroxycamphor], the other isomers and 3-(4-carboxybenzylidene)camphor were only minor metabolites excreted with urine. Enterohepatic circulation of glucuronides derived from the two major 4-MBC metabolites may explain the slow excretion of 4-MBC metabolites with urine and the small percentage of the administered doses recovered in urine.

来源:DrugBank

吸收、分配和排泄

• 分布容积

无药代动力学数据可用。

No pharmacokinetic data available.

来源:DrugBank

吸收、分配和排泄

• 清除

无药代动力学数据可用。

No pharmacokinetic data available.

来源:DrugBank

安全信息

• TSCA：
  Yes

制备方法与用途

生物活性

4-甲基苯基丙烯基莰烷（4-MBC；Enzacamene）是一种有机樟脑衍生物，广泛应用于化妆品行业，用以保护皮肤免受紫外线的伤害，尤其是紫外线B辐射。

用途

作为一种油溶性UV-B吸收剂，只需少量添加即可显著提高SPF值。此外，它还能作为Parsol 1789的有效光稳定剂。

反应信息

• 作为反应物：
  描述：

  (E)-rac-1,7,7-trimethyl-3-(4-methyl-benzylidene)-bicyclo[2.2.1]heptan-2-one 在 5%-palladium/activated carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 生成 1,7,7-trimethyl-3-(4-methylbenzyl)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  ANTIOXIDANTS

  摘要：

  本发明涉及使用化合物的公式（X-Ar-Y），其中X和Y分别独立地选择自组H，C-1-8烷基和公式（Ia），（Ib）或（Ic）所示的组，以及在说明书中定义的其他组，作为抗氧化剂。本发明还涉及相应的新化合物和制剂以及相应的化合物和制剂的生产方法。

  公开号：

  US20090098072A1

文献信息

• PHOTOPROTECTIVE COMPOSITIONS COMPRISING PHOTOSENSITIVE 1,3,5-TRIAZINE COMPOUNDS, DIBENZOYLMETHANE COMPOUNDS AND SILICEOUS S-TRIAZINES SUBSTITUTED WITH TWO AMINOBENZOATE OR AMINOBENZAMIDE GROUPS
  申请人：L'OREAL

  公开号：US20170135933A1

  公开（公告）日：2017-05-18

  UV-photoprotective, topically applicable cosmetic/dermatological compositions contain: (a) at least one dibenzoylmethane compound, (b) at least one 1,3,5-triazine compound that is photosensitive in the presence of a dibenzoylmethane compound, and (c) at least one siliceous s-triazine compound substituted with two aminobenzoate or aminobenzamide groups, or a tautomeric form thereof, the 1,3,5-triazine compounds being improvedly photostable in such compositions.

  UV-光保护，可局部应用的化妆品/皮肤科组合物包含： (a) 至少一种二苯甲酮化合物， (b) 至少一种1,3,5-三嗪化合物，在二苯甲酮化合物存在时对光敏感，以及 (c) 至少一种含有两个氨基苯甲酸酯或氨基苯酰胺基团的硅质s-三嗪化合物，或其互变异构体，这些1,3,5-三嗪化合物在这种组合物中具有改进的光稳定性。
• Flavonoid derivative
  申请人：Buchholz Herwig

  公开号：US20070134172A1

  公开（公告）日：2007-06-14

  The invention relates to a novel flavonoid derivative, to an extract comprising the flavonoid derivative, to the cosmetic and pharmaceutical use thereof, to preparations comprising the flavonoid derivative or extract, and to a process for the preparation of the flavonoid derivative or extract.

  这项发明涉及一种新型黄酮衍生物，一种包含该黄酮衍生物的提取物，以及其在化妆品和药用方面的使用，包括含有该黄酮衍生物或提取物的制剂，以及一种制备该黄酮衍生物或提取物的方法。
• Copolymers Based on N-Vinylpyrrolidone and Branched Aliphatic Carbonxylic Acids, and Their Use as Solubilizers
  申请人：Angel Maximilian

  公开号：US20080200564A1

  公开（公告）日：2008-08-21

  Copolymers comprising: (a) 60 to 99% by weight of at least one monomer selected from the group consisting of N-vinyllactams, N-vinylamides, and mixtures thereof; (1) 1 to 40% by weight of at least one monomer selected from the group consisting of vinyl esters of aliphatic branched C 8 -C 30 -carboxylic acids; (c) 0 to 30% by weight of vinyl acetate; and (d) 0 to 39% by weight of at least one additional free-radically copolymnerizable monomer; wherein the % by weight content of components (a), (b), (c) and (d) totals 100%, and with the proviso that the total amount of component (b) and component (c) combined is 1 to 40% by weight based on the copolymer, are described along with methods of using such copolymers to solubilize substances which are insoluble in water, substances which are only sparingly soluble in water, and combinations thereof.

  共聚物包含：（a）60至99重量百分比的至少一种单体，选自N-乙烯基内酰胺、N-乙烯酰胺和它们的混合物；（b）1至40重量百分比的至少一种单体，选自支链的C8-C30脂肪族羧酸的乙烯酯；（c）0至30重量百分比的乙酸乙烯酯；和（d）0至39重量百分比的至少一种额外的自由基共聚单体；其中，组分（a）、（b）、（c）和（d）的重量百分比总和为100%，并且有条件规定组分（b）和组分（c）的总和基于共聚物为1至40重量百分比。还描述了使用这样的共聚物来增溶水不溶性物质、水微溶性物质以及它们的组合的方法。
• [EN] HEMI-AMINAL ETHERS AND THIOETHERS OF N-ALKENYL CYCLIC COMPOUNDS<br/>[FR] ÉTHERS ET THIOÉTHERS HÉMIAMINAUX DE COMPOSÉS CYCLIQUES N-ALCÉNYLIQUES
  申请人：ISP INVESTMENTS INC

  公开号：WO2014116560A1

  公开（公告）日：2014-07-31

  Described herein are hemi-aminal ethers and thioethers of N-alkenyl cyclic compounds that may be produced through a reaction comprising: (A) at least one first reactant represented by a structure (I), wherein X is a functionalized or unfunctionalized C1-C5 alkylene group optionally having one or more heteroatoms, and each R1, R2, and R3 is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl groups optionally having one or more heteroatoms, and (B) at least one second reactant having at least one hydroxyl moiety or thiol moiety. The hemi-aminal ethers and thioethers of N-alkenyl cyclic compounds may comprise a polymerizable moiety, in which case they may be left as-is or used to create homopolymers or non-homopolymers, or they may not comprise a polymerizable moiety. A wide variety of formulations may be created using the hemi-aminal ethers and thioethers of N-alkenyl cyclic compounds, including personal care, oilfield, and construction formulations.

  本文描述了可以通过反应制备的N-烯基环状化合物的半胺醚和硫醚，所述反应包括：（A）至少一个由结构（I）表示的第一反应物，其中X是一个官能化或非官能化的C1-C5烷基烯烃基团，可选地具有一个或多个杂原子，每个R1、R2和R3分别独立地选自氢和官能化和非官能化的烷基基团，可选地具有一个或多个杂原子；和（B）至少一个具有至少一个羟基基团或硫醇基团的第二反应物。N-烯基环状化合物的半胺醚和硫醚可能包括一个可聚合的基团，此时它们可以保持原样或用于制备同聚物或非同聚物，或者它们可能不包括可聚合的基团。可以使用N-烯基环状化合物的半胺醚和硫醚制备各种配方，包括个人护理、油田和建筑配方。
• [EN] TRIAZINE DERIVATIVES AS UV ABSORBERS<br/>[FR] DERIVES DE LA TRIAZINE UTILISES COMME ABSORBANTS U.V.
  申请人：CIBA SC HOLDING AG

  公开号：WO2004064797A1

  公开（公告）日：2004-08-05

  The present invention relates to new compounds of formula (I), wherein R1, R2, R3, R4, R5, R6, R7, and R8 independently from each other are hydrogen; C1-C18alkyl; C2-C18alkenyl; C5-C7,cycloalkyl; C1-C6alkylene-C5- C7,cycloalkyl; R9 is hydrogen; C1-C18alkyl; C2-C18alkenyl; C5-C7cycloalkyl; C1-C6alkylene-C5-C7cycloalkyl; C6-C10aryl; A is-S-; -O- or -NR10-, wherein R10 has the same meanings as R9; X is COOR11; CONR12R13; SO3,R14; or SO2NR15R16, wherein R11, R12,R13, R14,R15, and R16, have independently from each other the same meanings as R9; to their preparation and to their use as UV absorbers in cosmetic and pharmaceutical formulations.

  本发明涉及公式（I）的新化合物，其中R1、R2、R3、R4、R5、R6、R7和R8彼此独立地是氢；C1-C18烷基；C2-C18烯基；C5-C7环烷基；C1-C6烷基-C5-C7环烷基；R9是氢；C1-C18烷基；C2-C18烯基；C5-C7环烷基；C1-C6烷基-C5-C7环烷基；C6-C10芳基；A是-S-；-O-或-NR10-，其中R10具有与R9相同的含义；X是COOR11；CONR12R13；SO3R14；或SO2NR15R16，其中R11、R12、R13、R14、R15和R16彼此独立地具有与R9相同的含义；以及它们的制备和它们作为化妆品和药用配方中的紫外线吸收剂的用途。