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Enne oil

中文名称
——
中文别名
——
英文名称
Enne oil
英文别名
hexadecanoic acid;(9Z,12Z)-octadeca-9,12-dienoic acid;octadecanoic acid;(Z)-octadec-9-enoic acid
Enne oil化学式
CAS
——
化学式
C70H134O8
mdl
——
分子量
1103.8
InChiKey
UAKWPJAYOBUUBC-CDLHYPJOSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    23.88
  • 重原子数:
    78
  • 可旋转键数:
    59
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.86
  • 拓扑面积:
    149
  • 氢给体数:
    4
  • 氢受体数:
    8

ADMET

代谢
芝麻油中存在的一种单酚类抗氧化剂Sesamol (II)容易与亚硝酸盐发生反应。在稀溶液中,当II过量时,它能迅速并完全去除亚硝酸盐,生成等量的3,4-亚甲二氧基-6-亚硝基苯酚(III);在pH 2.0时速率最快,其次是pH 3.0和4.0。在稀溶液中,当亚硝酸盐过量时,形成的III的量与损失的亚硝酸盐量相对应,但少于最初存在的II的量,可能发生了一些副反应。化合物II阻止了二甲胺的N-亚硝化反应,就像对苯二酚和L-抗坏血酸一样,或者在特定条件下加速了该反应。化合物III对N-亚硝化反应显示了催化作用。用作食品添加剂的亚硝胺是潜在的致癌物质。
Sesamol (II), a monophenolic antioxidant present in sesame oil, interacted readily with nitrite. In dilute aqueous solutions with II in excess, it rapidly and completely removed nitrite to produce an equivalent amount of 3,4-methylenedioxy-6-nitrosophenol (III); the rate was fastest at pH 2.0, followed by pH 3.0 and 4.0. In dilute solutions with nitrite in excess, the amount of III formed, which corresponded well to that of nitrite lost, was less than that of II initially present, and some side reactions may have occurred. Compound II prevented the N-nitrosation of dimethylamine, as did pyrocatechol and L-ascorbic acid, or accelerated the reaction, depending upon the conditions. Compound III showed a catalytic effect on the N-nitrosation. (Nitrosamines used as food additives are potential carcinogens.)
来源:Hazardous Substances Data Bank (HSDB)
代谢
尿液排出的芝麻酚儿茶酚代谢物... 大约在22%到39%之间,主要是以葡萄糖醛酸苷和硫酸盐形式。/芝麻酚/
The urinary excretion of the sesamin catechol metabolite... ranges from about 22% to 39%, mostly in the glucuronide and sulfate forms. /Sesamin/
来源:Hazardous Substances Data Bank (HSDB)
代谢
摄入后,一些芝麻素从小肠吸收,一些被肠内微生物转化为哺乳动物木脂素肠内酯(ENT)和较少程度的哺乳动物木脂素肠二醇(END)... 一些芝麻素也从小肠吸收并最终到达肝脏,在肝脏中发生氧化转化和去甲基化,形成多种羟基化儿茶酚代谢物... 儿茶酚代谢物可能会通过胆汁排出,然后在大肠的肠内菌群作用下转化为ENT和ENL。/芝麻素/
After ingestion, some sesamin is absorbed from the small intestine and some is converted by the intestinal microflora... to the mammalian lignan enterolactone (ENT), and to a lesser degree to the mammalian lignan, enterodiol (END)... Some sesamin is also absorbed in the small intestine and winds up in the liver where... undergoes oxidative transformation and demethylation to form a number of hydroxylated catechol metabolites... The catechol metabolites may get excreted in the bile and then get metabolized by the intestinal flora of the large intestine to ENT and ENL. /Sesamin/
来源:Hazardous Substances Data Bank (HSDB)
代谢
6名参与者(3名男性,3名女性;年龄22至32岁)服用了一次芝麻油(含508毫摩尔芝麻素,主要芝麻油木脂素)的单一剂量,并收集了他们的尿液,分为四个12小时时段。尿液样本用β-葡萄糖醛酸酶/硫酸酯酶处理,并用氯仿提取。氯仿提取物中的主要尿液芝麻素代谢物被鉴定为(1R,2S,5R,6S)-6-(3,4-二羟基苯基)-2-(3,4-亚甲二氧基苯基)-3,7-二氧杂双环[3,3,0]辛烷,使用核磁共振(NMR)和质谱。芝麻素儿茶酚代谢物的排泄量占摄入剂量的22.3%至38.6%(平均值±标准差,29.3±5.6),主要在摄入后前12小时内发生。
6 participants (3 males, 3 females; 22 to 32 years old) took a single dose of Sesame oil (508 mmol sesamin, major sesame oil lignan) and their urine was collected for four 12-hour periods. The urine samples were treated with b-glucuronidase/ sulfatase and extracted with chloroform. The major urinary sesamin metabolite in the chloroform extract was characterized as (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4- methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane using nuclear magnetic resonance (NMR) and mass spectroscopy. The excretion of the sesamin catechol metabolite ranged from 22.3% to 38.6% (mean+/-SD, 29.3+/-5.6) of the ingested dose and happened mainly in the first 12 hours after ingestion.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
识别和使用:芝麻油是从芝麻(Sesamum indicum)种子中获得的植物油。它在原产国被广泛用作食用油。芝麻油在美国目前的药物用途是作为注射药物或静脉滴注溶液的“医疗载体”。它还被化妆品行业用作载体或载体配方的一部分。人类暴露和毒性:芝麻油不是皮肤刺激物、皮肤致敏物或光敏剂。然而,它可能导致婴儿和幼儿严重的IgE介导的食物过敏反应:主要临床表现为荨麻疹/血管性水肿,一些患者的首发症状是过敏性休克;他们全都在1岁以下。一些患者被发现对其他食物过敏,还识别出其他异位性疾病。三名患者在1-2年内“长大成人”他们的过敏。在芝麻过敏的成年人中,报告称在食用芝麻油后,面部出现针扎般的感觉,随后出现寒战、颤抖和腹部绞痛。动物研究:在对大鼠进行芝麻油给药并观察一年后,没有观察到与治疗相关的变化。芝麻油在动物中不是致癌物也不是致畸物。然而,充气芝麻油是一种轻微的致癌物。芝麻油喂食幼虫在黑腹果蝇(Drosophila melanogaster)中诱导体细胞突变,但在Ames试验中,无论是否添加S9活化剂,对鼠伤寒沙门氏菌TA98和TA100均无诱变性。然而,从240°C和260°C烤制温度制备的油脂的极性部分在添加S9活化剂时对S. typhimurium TA98表现出弱的诱变性。此外,与那些喂食含有3%芝麻油饮食的小鼠相比,接受9%或12%芝麻油饮食8周的小鼠呈现出统计学上显著增加的黄曲霉毒素B1诱导的畸变率。
IDENTIFICATION AND USE: Sesame oil is a vegetable oil obtained from the seeds of Sesamum indicum. It is widely used as edible oil in the countries of origin. A current pharmaceutical use for sesame oil in the US is as a "medical carrier" for injected drug or intravenous drip solutions. It also is used as a carrier or as part of a carrier formulation by the cosmetics industry. HUMAN EXPOSURE AND TOXICITY: Sesame oil is not a skin irritant, skin sensitizer, or photoallergen. However, it could cause severe IgE-mediated food allergic reactions among infants and young children: the main clinical manifestation was urticaria/angiedema , anaphylaxis was the presenting symptom in some patients; all of them were younger than 1 year. Some patients were found to be allergic to other foods, and other atopic diseases were identified as well. Three patients 'outgrew' their allergy within 1-2 years. In adults with sesame allergy, a pin and- needle sensation on the face, followed by the onset of chills, shakiness, and abdominal cramps, were reported after eating sesame oil. ANIMAL STUDIES: No treatment-related changes were observed in groups of rats following administration of sesame oil and observation for one year. Sesame oil was not carcinogenic or teratogenic in animals. However aerated sesame oil was a mild carcinogen. Sesame oil fed to larvae induced somatic mutations in Drosophila melanogaster, but it was not mutagenic in Ames test with Salmomella typhimurium TA98 and TA100 with or without S9 activation. However, the polar part of oils prepared from 240 and 260 °C of roasting temperatures showed weak mutagenicity to S. typhimurium TA98 with S9 activation. Furthermore, mice receiving either 9% or 12% sesame oil in their diet for 8 weeks presented a statistically increased aflatoxin B1-induced aberration rate as compared to those given a diet containing 3% sesame oil.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
双氯芬酸:芝麻木质素sesamol已被证明可以减轻大鼠因双氯芬酸引起的急性胃损伤... /Sesamol/
Diclofenac: The sesame lignan sesamol has been shown to attenuate the acute gastric injury in rats caused by the diclofenac... /Sesamol/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
抗生素:与芝麻种子木质素同时使用可能减少由芝麻种子木质素产生的人体木质素肠内酯(ENT)和肠二醇(END)。/芝麻种子木质素/
Antibiotics: Concomitant use with sesame seed lignans may decrease the production of the mammalian lignans enterolactone (ENT) and enterodiol (END) from sesame seed lignans. /Sesame seed lignans/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
芝麻种子木质素中的芝麻素和芝麻醇(136毫克)在一项人体研究中被发现可以减少共同给药的γ-生育酚的尿排泄。/芝麻种子木质素/
A single dose of the sesame seed lignans sesamin and sesamolin (136 mg) was found to reduce the urinary excretion of co-administered gamma-tocopherol in a human study. /Sesame seed lignans/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
膳食芝麻素、二十二碳六烯酸(DHA)和二十碳五烯酸(EPA)在大鼠体内协同增加了参与肝脏过氧化物酶体脂肪酸氧化的酶的基因表达... /芝麻素/
Dietary sesamin, docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) synergistically increased the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rat... /Sesamin/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在这个研究中,检查了大鼠体内精炼芝麻油木质素(芝麻素和表芝麻素)的分布和代谢。在大鼠的饮食中加入了含有0.5%(按重量计)芝麻木质素(芝麻素和表芝麻素)以及5%(按重量计)玉米油或富含二十碳五烯酸(EPA)的油,持续8周。在大鼠给药8周后,大鼠肝脏中芝麻素和表芝麻素的浓度非常低;两者都小于0.5微克/克肝脏。这两种情况在两种油组中都有观察到,尽管饮食油的脂肪酸组成完全不同。芝麻素和表芝麻素之间的淋巴吸收没有显著差异。为了调查大鼠体内芝麻素和表芝麻素的分布,在大鼠给药后24小时内,测定了组织和血清中芝麻素和表芝麻素的浓度。芝麻素和表芝麻素可能首先被肝脏吸收,然后传输到其他组织(肺、心脏、肾脏和大脑)。它们在给药后24小时内从体内消失。芝麻素和表芝麻素之间的淋巴吸收没有显著差异,但在所有组织和血清中,芝麻素的量显著低于表芝麻素。这些结果表明,芝麻素的淋巴吸收与表芝麻素相同,但芝麻素随后被肝脏代谢得更快。芝麻素和表芝麻素。
In this study, ...the distribution and metabolism of refined sesame oil lignans (sesamin and episesamin) in rat /was examined/. For 8 wk rats were fed the diet including 0.5% (w/w) sesame lignans (sesamin and episesamin) with 5% (w/w) corn oil or eicosapentaenoic acid (EPA)-rich oil. The concentrations of sesamin and episesamin in rat liver after their administration for 8 wk were very low; both of them were <0.5 ug/g liver. These were observed in both oil groups although the fatty acid compositions of dietary oils were completely different. No significant difference existed in lymphatic absorption between sesamin and episesamin. To investigate the distribution of sesamin and episesamin in rats, the concentrations of sesamin and episesamin were determined in tissues and serum within 24 hr after administration to rats. Sesamin and episesamin may be, at first, incorporated into the liver and then transported to the other tissues (lung, heart, kidney, and brain). They are lost from the body within 24 hr after administration. There was no significant difference in lymphatic absorption between sesamin and episesamin, but the amount of sesamin was significantly lower than that of episesamin in all tissues and serum. These results suggest that sesamin is absorbed in lymph the same as episesamin, but that sesamin is subsequently metabolized faster by the liver. /Sesamin and episesamin/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在实验1中,4周大的老鼠被喂食了仅含α-生育酚或同时含有α-和γ-生育三烯酚的饮食。在实验2中,研究了饮食中芝麻种子对喂食了生育酚和生育三烯酚的老鼠体内生育酚和生育三烯酚浓度的影响。在这两个实验中,老鼠被喂食实验性饮食共8周。在喂食了生育三烯酚的老鼠的脂肪组织和皮肤中积累了α-和γ-生育三烯酚,但在血浆或其他组织中没有。饮食中的芝麻种子提高了(P<0.05)脂肪组织和皮肤中的生育三烯酚浓度,但并未影响它们在其他组织或血浆中的浓度。喂食了γ-生育酚的老鼠的所有组织和血浆中的γ-生育酚浓度非常低,但通过喂食芝麻种子在许多组织中提高了(P<0.05)。这些数据表明,维生素E异构体的运输和组织摄取是不同的。饮食中的芝麻种子可以提高生育酚和生育三烯酚的浓度。/芝麻种子/
... In experiment 1, rats (4-wk-old) were fed the diet with alpha-tocopherol alone or with alpha- and gamma-tocotrienols. In experiment 2, the effect of dietary sesame seeds on tocopherol and tocotrienol concentrations in rats fed the diet with tocopherol and tocotrienol was studied. The rats were fed the experimental diet for 8 wk in both experiments. alpha- and gamma-Tocotrienols accumulated in the adipose tissue and skin, but not in plasma or other tissues, of the rats fed tocotrienols. Dietary sesame seeds elevated (P<0.05) tocotrienol concentrations in the adipose tissue and skin, but did not affect their concentrations in other tissues or in plasma. The gamma-tocopherol concentration in all tissues and plasma of rats fed gamma-tocopherol was extremely low but was elevated (P<0.05) in many tissues by feeding sesame seeds. These data suggest that the transport and tissue uptake of vitamin E isoforms are different. Dietary sesame seeds elevate the concentrations of both tocopherols and tocotrienols. /Sesame seeds/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
尿液排出的大豆苷元儿茶酚代谢物...的范围大约在22%到39%之间,主要是以葡萄糖醛酸苷和硫酸盐形式存在。/大豆苷元/
The urinary excretion of the sesamin catechol metabolite... ranges from about 22% to 39%, mostly in the glucuronide and sulfate forms. /Sesamin/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
对年轻成年白化病大鼠进行分组,分别通过皮下(SC)或腹腔内(IP)注射芝麻油,并在测试约1年后处死。在62毫升IP组中,一只雌性大鼠的肺实质内沉积了大量芝麻油,这被认为是芝麻油在IP给药后系统分布的证据。总体而言,芝麻油在IP或SC注射后倾向于在大鼠体内迁移。在SC注射后,测试物质倾向于在腹部下侧的SC组织中积聚。在与芝麻油IP给药的所有大鼠组中,也观察到了SC组织中类似的分布模式。
Groups of young adult albino rats were dosed, either subcutaneously (SC) or intraperitoneally (IP), with sesame oil, and killed after approximately 1 year on test. One female rat in the 62-mL IP group had a massive deposition of sesame oil within the parenchyma of the lung, which was considered evidence of systemic distribution of sesame oil after IP dosing. Overall, there was a tendency for sesame oil to migrate within the body of the rat following IP or SC injection. Following SC injection, the test substance tended to pool in the SC tissue of the ventral abdomen. A similar pattern of distribution in the SC tissue was noted in all groups of rats dosed IP with sesame oil.
来源:Hazardous Substances Data Bank (HSDB)