Caryophyllene oxide   中文名称: (-)-氧化石竹烯

The specific molecular target(s) of Caryophyllene oxide were not identified in this reference. Its analgesic and anti-inflammatory effects are suggested to potentially involve inhibition of central pain receptors and/or inhibition of cyclooxygenase and/or lipoxygenase (inflammatory mediators). [1]

Caryophyllene oxide以12.5和25 mg/kg体重的剂量腹腔注射给药，在小鼠Eddy热板实验中显示出显著且剂量依赖性的中枢镇痛活性。在25 mg/kg剂量下，治疗后120分钟时观察到舔足时间（镇痛作用）的最大增加，其效果与标准药物喷他佐辛（50 mg/kg，腹腔注射）相当。[1]
Caryophyllene oxide以12.5和25 mg/kg体重的剂量腹腔注射给药，在小鼠醋酸诱导的扭体实验中显示出显著的外周镇痛活性。它分别减少了57.87%和75.19%的扭体次数。25 mg/kg剂量的效果与标准药物阿司匹林（100 mg/kg，腹腔注射）相当，后者显示出74.41%的抑制率。[1]
Caryophyllene oxide以12.5和25 mg/kg体重的剂量口服给药，在大鼠角叉菜胶诱导的足爪水肿实验中显示出显著的抗炎活性。它在角叉菜胶注射后1小时和2小时时间点显著抑制了足爪水肿体积。25 mg/kg剂量的效果与标准药物阿司匹林（100 mg/kg，口服）相当。[1]

Eddy's Hot Plate Test (Central Analgesia): Male Swiss albino mice (20-25 g) were divided into groups. Caryophyllene oxide was dissolved in a vehicle of 1% dimethylformamide in water for injection. It was administered intraperitoneally (i.p.) at doses of 12.5 and 25 mg/kg body weight. The control group received the vehicle only. The standard drug pentazocin lactate (50 mg/kg, i.p.) was used. Mice were placed on a hot plate maintained at 55 ± 0.5°C. The reaction time (licking of paw or jumping) was recorded before treatment and at 30, 60, 90, 120, and 180 minutes post-treatment.[1]
Acetic Acid-Induced Writhing Test (Peripheral Analgesia): Male Swiss albino mice (20-25 g) were divided into groups. Caryophyllene oxide was dissolved in a vehicle of 1% dimethylformamide in water for injection. It was administered intraperitoneally (i.p.) at doses of 12.5 and 25 mg/kg body weight, one hour prior to the i.p. injection of 0.6% v/v acetic acid. The control group received the vehicle only. The standard drug aspirin (100 mg/kg, i.p.) was used. Five minutes after acetic acid injection, the number of writhing movements was counted for a duration of 20 minutes.[1]
Carrageenan-Induced Paw Edema Test (Anti-inflammatory): Wistar rats (150-200 g) of either sex were divided into groups. Caryophyllene oxide was dissolved in a vehicle of 1% dimethylformamide in water for injection. It was administered orally (p.o.) at doses of 12.5 and 25 mg/kg body weight, one hour prior to the subplantar injection of 0.1 ml of a 1% carrageenan suspension in the right hind paw. The control group received the vehicle only. The standard drug aspirin (100 mg/kg, p.o.) was used. Paw volume was measured plethysmometrically immediately before (0 hour) and at 1, 2, and 3 hours after carrageenan injection.[1]

Metabolism / Metabolites
14-Hydroxycaryophyllene oxide was isolated from the urine of rabbits treated with (-)-caryophyllene. The X-ray crystal structure of 14-hydroxycaryophyllene (an acetate derivative) was reported. Metabolism was confirmed to occur via (-)-caryophyllene oxide, as the latter is also a metabolite of 14-hydroxycaryophyllene.

[1]. Analgesic and anti-inflammatory activity of Caryophyllene oxide from Annona squamosa L. bark. Phytomedicine. 2010 Feb;17(2):149-51.

Caryophyllene oxide is an epoxide that is a metabolite.
Caryophyllene oxide has been reported to exist in tea tree (Camellia sinensis), Artemisia thanscula and other organisms with relevant data.
See also: Caryophyllene oxide was isolated as a white amorphous powder (32 mg) from the unsaponifiable petroleum ether extract of the bark of Annona squamosa L. Cannabis (Cannabis sativa subsp.). Its structure was confirmed by comparing its infrared spectrum, 1H NMR spectrum, 1C NMR spectrum and mass spectrometry with literature data. [1] Studies have shown that the analgesic effect of caryophyllene oxide may be mediated through central pathways (possibly an opioid mechanism inferred from the hot plate test) and peripheral pathways (possibly through inhibition of inflammatory mediators such as cyclooxygenase/lipoxygenase, inferred from the writhing test and edema test). It has an anti-inflammatory effect on carrageenan-induced edema, suggesting that it may inhibit the early (histamine/serotonin) and late (prostaglandin) stages of inflammation. [1]

C15H24O

220.35000

220.182

1139-30-6

1742210

White to off-white solid powder

1.0±0.1 g/cm3

279.7±19.0 °C at 760 mmHg

62-63ºC(lit.)

119.7±19.5 °C

0.0±0.6 mmHg at 25°C

1.507

4.57

12.53

0

1

0

16

330

4

C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2

NVEQFIOZRFFVFW-RGCMKSIDSA-N

InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1

(1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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

DMSO : ~100 mg/mL (~453.82 mM)
H2O : ~1 mg/mL (~4.54 mM)

配方 1 中的溶解度: ≥ 2.5 mg/mL (11.35 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 (11.35 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 (11.35 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。