trans-Cinnamaldehyde   中文名称: 反式肉桂醛

沙门氏菌是反式肉桂醛-β-环糊精复合物的目标。以及李斯特菌属物种。根据参考文献[1]，最低抑制剂量为10和20mg/mL。

Absorption, Distribution and Excretion
Cinnamaldehyde is 52% absorbed through the skin and shown to be rapidly absorbed from the gut.
Cinnamaldehyde is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 69–98% of the dose of cinnamaldehyde was recovered in the urine and feces within 24 h.
The bioavailability of microencapsulated cinnamaldehyde (CNMA) was investigated in male F344 rats. Rats were gavaged with CNMA in corn oil using either microencapsulated or the neat chemical at doses of 50, 250, and 500 mg/kg. No differences between the two formulations at any of the doses were found in either CNMA blood concentration profiles or in the rate of urinary hippuric acid excretion. Both formulations showed a low bioavailability (< 20%) at 250 and 500 mg/kg. Regardless of the formulation used, oral gavage of CNMA significantly increased the urinary excretion of hippuric acid. About 75% of the dose of CNMA was metabolized to hippuric acid and recovered in the urine. The total amount of hippuric acid recovered in a 50-hr urinary collection correlated well with the CNMA dose. The data suggest that there was complete release of CNMA from the microcapsules and that microencapsulation of CNMA does not affect its bioavailability or its metabolism ...
/Cinnamaldehyde is/ presumably oxidized in vivo to cinnamic acid, which is excreted in urine as benzoic and hippuric acids.
After ip admin of cinnamic aldehyde to rats, urinary thio ether excretion amounted to 6.5% of dose.
Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.
For more Absorption, Distribution and Excretion (Complete) data for CINNAMALDEHYDE (7 total), please visit the HSDB record page.

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Metabolism / Metabolites
The metabolism of trans-[3-14C]cinnamaldehyde was investigated in male and female Fischer 344 rats and CD1 mice at doses of 2 and 250 mg/kg bw given by ip injection and in males at 250 mg/kg by oral gavage. Some 94% of the administered dose was recovered in the excreta in 72 hr in both species with most (75-81%) present in the 0-24-hr urine. Less than 2% of the administered dose was found in the carcasses at 72 hr after dosing. Urinary metabolites were identified by their chromatographic characteristics. In both species the major urinary metabolite was hippuric acid accompanied by 3-hydroxy-3-phenylpropionic acid, benzoic acid and benzoyl glucuronide. The glycine conjugate of cinnamic acid was formed to a considerable extent only in the mouse. The oxidative metabolism of cinnamaldehyde essentially follows that of cinnamic acid, by beta-oxidation analogous to that of fatty acids. Apart from the metabolites common to cinnamic acid and cinnamaldehyde, 7% of 0-24-hr urinary 14C was accounted for by two new metabolites in the rat and three in the mouse, which have been shown in other work to arise from a second pathway of cinnamaldehyde metabolism involving conjugation with glutathione. The excretion pattern and metabolic profile of cinnamaldehyde in rats and mice are not systematically affected by sex, dose size and route of administration. The data are discussed in terms of their relevance to the safety evaluation of trans-cinnamaldehyde, particularly the validity or otherwise of extrapolation of toxicity data from high to low dose. /trans-Cinnamaldehyde/
To evaluate the extent of cinnamaldehyde and cinnamic alcohol metabolism in human skin and provide evidence for the role of cutaneous alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) in such metabolism ... the extent of cinnamic alcohol and aldehyde metabolism was investigated in human skin homogenates and sub-cellular fractions ... Studies were conducted in the presence and absence of the ADH/cytochrome P450 inhibitor 4-methylpyrazole and the cytosolic ALDH inhibitor, disulfiram. Differential metabolism of cinnamic alcohol and cinnamaldehyde was observed in various subcellular fractions: skin cytosol was seen to be the major site of cinnamic compound metabolism. Significant metabolic inhibition was observed using 4-methylpyrazole and disulfiram in whole skin homogenates and cytosolic fractions only ... This study has demonstrated that cutaneous ADH and ALDH activities, located within defined subcellular compartments, play important roles in the activation and detoxification of CAlc and CAld in skin ...
Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.
Identification of 2 sulfur containing urinary metabolites of cinnamic aldehyde in rat which are 3-S-(N-acetylcysteinyl)-3-phenylpropyl alcohol and 3-S-(N-acetylcysteinyl)-3-phenylpropionic acid.
For more Metabolism/Metabolites (Complete) data for CINNAMALDEHYDE (6 total), please visit the HSDB record page.
Cinnamaldehyde is a known human metabolite of cinnarizine.
Cinnamaldehyde is converted to cinnamoyl-CoA by cinnamoyl-CoA reductase.

Toxicity Summary
Cinnamaldehyde is an allergen. The physiologic effect of cinnamaldehyde is by means of increased histamine release and cell-mediated immunity.

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Toxicity Data
LD50: 3400 mg/kg (rat, oral)

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Interactions
The Japanese medaka (Oryzias latipes) was used in the medaka embryo-larval assay (MELA) to determine possible adverse developmental effects of ethanol and the spice component, cinnamaldehyde (CAD) ... Medaka were exposed to ethanol at 100 mM, CAD at 10, 1.0, 0.67 or 0.50 mM, to ethanol and CAD combined, or were non-treated controls. Ethanol at 100 mM was without effect. CAD alone at 10 mM and 1.0 mM was lethal by 1 dpf. Embryos exposed to 100 mM ethanol and 0.67 mM CAD exhibited cardiovascular and pigmentation defects and delayed hatching. Embryos exposed to 0.50 mM CAD alone had less severe cardiovascular problems as compared to the combined ethanol and CAD treatment. Taken together the results indicate that the combined effects of ethanol and CAD are greater than the individual effects and indicate the need to monitor effluents in fish nursery areas to protect natural fish populations.

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Non-Human Toxicity Values
LD50 Rat oral 3400 mg/kg
LD50 Mouse oral 200 mg/kg
LD50 Mouse ip 200 mg/kg
LD50 Mouse iv 75 mg/kg
For more Non-Human Toxicity Values (Complete) data for CINNAMALDEHYDE (8 total), please visit the HSDB record page.

[1]. A Facile One-Pot Synthesis of Amino Furans Using Trans-Cinnamaldehyde in the Presence of Nucleophilic Isocyanides. Acta Chimica Slovenica 54(3), 341-350, (2007).

[2]. Polysaccharide-based multilayered antimicrobial edible coating enhances quality of fresh-cut papaya.LWT--Food Science and Technology 47(1), 39-45, (2012).

(E)-cinnamaldehyde is the E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes. It has a role as a hypoglycemic agent, an EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor, a vasodilator agent, an antifungal agent, a flavouring agent, a plant metabolite and a sensitiser. It is a 3-phenylprop-2-enal and a member of cinnamaldehydes.
Cinnamaldehyde is a naturally occurring flavonoid that gives the spice cinnamon its flavour and odour. It occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum such as camphor and cassia. Sensitivity to cinnamaldehyde may be identified with a clinical patch test.
Cinnamaldehyde is a Standardized Chemical Allergen. The physiologic effect of cinnamaldehyde is by means of Increased Histamine Release, and Cell-mediated Immunity.
Cinnamaldehyde has been reported in Curcuma xanthorrhiza, Alpinia latilabris, and other organisms with data available.
Cinnamaldehyde is the aldehyde that gives cinnamon its flavor and odor. Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum like camphor and cassia. These trees are the natural source of cinnamon, and the essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde is also used as a fungicide. Proven effective on over 40 different crops, cinnamaldehyde is typically applied to the root systems of plants. Its low toxicity and well-known properties make it ideal for agriculture. To a lesser extent, cinnamaldehyde is an effective insecticide, and its scent is also known to repel animals like cats and dogs. Cinnamaldehyde is also known as a corrosion inhibitor for steel and other ferrous alloys in corrosive fluids. It can be used in combination with additional components such as dispersing agents, solvents and other surfactants. Concentrated cinnamaldehyde is a skin irritant, and the chemical is toxic in large doses, but no agencies suspect the compound is a carcinogen or poses a long-term health hazard. Most cinnamaldehyde is excreted in urine as cinnamic acid, an oxidized form of cinnamaldehyde.
Cinnamaldehyde is a metabolite found in or produced by Saccharomyces cerevisiae.

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Drug Indication
Cinnamaldehyde is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

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Therapeutic Uses
/EXPL THER/ Cinnamonum zeylanicum (cinnamon) is widely used in traditional system of medicine to treat diabetes in India. The present study was carried out to isolate and identify the putative antidiabetic compounds ... Cinnamaldehyde was administered at different doses (5, 10 and 20 mg/kg bw) for 45 days to streptozotocin (STZ) (60 mg/kg bw)-induced male diabetic wistar rats. It was found that plasma glucose concentration was significantly (p<0.05) decreased in a dose-dependent manner (63.29%) compared to the control. In addition, oral administration of cinnamaldehyde (20 mg/kg bw) significantly decreased glycosylated hemoglobin (HbA(1C)), serum total cholesterol, triglyceride levels and at the same time markedly increased plasma insulin, hepatic glycogen and high-density lipoprotein-cholesterol levels. Also cinnamaldehyde restored the altered plasma enzyme (aspartate aminotransferase, alanine aminotransferase, lactate dehydrogenase, alkaline phosphatase and acid phosphatase) levels to near normal. Administration of glibenclamide, a reference drug (0.6 mg/kg bw) also produced a significant (p < 0.05) reduction in blood glucose concentration in STZ-induced diabetic rats. The results of this experimental study indicate that cinnamaldehyde possesses hypoglycemic and hypolipidemic effects in STZ-induced diabetic rats.

C₉H₈O

132.16

132.057

14371-10-9

637511

Colorless to light yellow liquid

1.0±0.1 g/cm3

246.8±9.0 °C at 760 mmHg

−9-−4 °C(lit.)

71.1±0.0 °C

0.0±0.5 mmHg at 25°C

1.577

2.12

17.07

0

1

2

10

121

0

O=C([H])/C(/[H])=C(\[H])/C1C([H])=C([H])C([H])=C([H])C=1[H]

KJPRLNWUNMBNBZ-QPJJXVBHSA-N

InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+

(E)-3-phenylprop-2-enal

transCinnamaldehyde; trans Cinnamaldehyde

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

注意： 请将本产品存放在密封且受保护的环境中（例如氮气保护），避免吸湿/受潮。

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~50 mg/mL (~378.33 mM)

配方 1 中的溶解度: ≥ 2.5 mg/mL (18.92 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入到400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 2.5 mg/mL (18.92 mM) (饱和度未知) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 3 中的溶解度: ≥ 2.5 mg/mL (18.92 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。