(±)-Dihydroactinidiolide
(Synonyms: (±)-二氢猕猴桃内酯) 目录号 : GC61714
(±)-Dihydroactinidiolide是一种红茶和烟草中的重要香气化合物，可从多种植物中分离出来。(±)-Dihydroactinidiolide可以由多酚氧化酶，脂氧合酶和黄嘌呤氧化酶的处理β-胡萝卜素形成。
Cas No.:15356-74-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(±)-Dihydroactinidiolide, an important aroma compound of black tea and tobacco, has been isolated from several plants. (±)-Dihydroactinidiolide can be formation from β-Carotene by the treatment of polyphenoloxidase, the lipoxygenase, and the xanthine oxidase[1][2].
[1]. Kaneko H, et, al. The Aroma of Cigar Tobacco. Part I. Isolation of 2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic Acid Lactone (Dihydroactinidiolide) from Ether Extract of Cigar Leaves. Agricultural and Biological Chemistry. 1968 Jou; 32(11): 1337-40. [2]. Bosser A, et, al. A Simple Way to (±)-Dihydroactinidiolide from β-Ionone Related to the Enzymic Co-oxidation of β-Carotene in Aqueous Solution. Biotechnology Progress. 1995 Jou; 11(6): 689-92.
| Cas No. | 15356-74-8 | SDF | |
| 别名 | (±)-二氢猕猴桃内酯 | ||
| Canonical SMILES | O=C1OC2(C)C(C(C)(C)CCC2)=C1 | ||
| 分子式 | C11H16O2 | 分子量 | 180.24 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.5482 mL | 27.7408 mL | 55.4816 mL |
| 5 mM | 1.1096 mL | 5.5482 mL | 11.0963 mL |
| 10 mM | 0.5548 mL | 2.7741 mL | 5.5482 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Online gas chromatography combustion/pyrolysis-isotope ratio mass spectrometry (HRGC-C/P-IRMS) of (+/-)-Dihydroactinidiolide from tea ( Camellia sinensis ) and rooibos tea ( Aspalathus linearis )
J Agric Food Chem 2009 Jul 8;57(13):5899-902.PMID:19514730DOI:10.1021/jf9009125.
Online capillary gas chromatography-isotope ratio mass spectrometry in both the combustion and the pyrolysis modes (HRGC-C/P-IRMS) was employed to perform authentication studies of the flavoring agent (+/-)-Dihydroactinidiolide. Thus, the delta(13)C(V-PDB) and delta(2)H(V-SMOW) values of synthetic (ex synthetic beta-ionone and natural beta-carotene) as well as enzymatically (ex synthetic and natural beta-carotene) produced references were studied in comparison with those of the natural substance isolated from black (n = 17) and green teas (n = 6) ( Camellia sinensis ) as well as Rooibos tea ( Aspalathus linearis ) (n = 7). The isotope values determined for both the synthetic and enzymatically produced samples of (+/-)-Dihydroactinidiolide reflected the influence of the origin of their educts. Hence, in cases when synthetic educts were used, the delta(13)C(V-PDB) and delta(2)H(V-SMOW) values ranged from -27.0 to -28.4 per thousand and from -28 to -169 per thousand, respectively, whereas the use of natural educts led to ranges from -30.3 to -31.6 per thousand and from -154 to -228 per thousand, respectively. As to the tea samples, delta(13)C(V-PDB) and delta(2)H(V-SMOW) values ranging from -29.0 to -34.1 per thousand and from -153 to -274 per thousand, respectively, were recorded for (+/-)-Dihydroactinidiolide from black and green teas, whereas that from Rooibos tea showed (2)H/(1)H ratios ranging from -189 to -210 per thousand as well as slightly enriched values in the (13)C/(12)C ratios ranging from -24.4 to -27.1 per thousand.
Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology
J Org Chem 1998 Jan 9;63(1):118-121.PMID:11674051DOI:10.1021/jo971528y.
The total synthesis of the naturally occurring bicyclic lactones (R)-Dihydroactinidiolide and (R)-actinidiolide is presented. The key step in the syntheses is the copper(II)-bisoxazoline-catalyzed hetero-Diels-Alder reaction of a cyclic diene with ethyl glyoxylate giving the hetero-Diels-Alder product in high yield and with very high regio-, diastereo-, and enantioselectivity. The total syntheses proceed via an intermediate, which also has the potential for a series of other natural products. The structure of the key intermediate is confirmed by X-ray analysis.
Characterization of key aroma compounds and enantiomer distribution in Longjing tea
Food Chem 2021 Nov 1;361:130096.PMID:34023691DOI:10.1016/j.foodchem.2021.130096.
By comparing the enantiomers of authentic Longjing tea, the authenticity of Longjing tea can be effectively distinguished. In this study, 18 enantiomers were identified using a chiral column. At the same time, the unique enantiomer ratio (ER) of Longjing tea (LG1, LG2, LG3, LG4, LG5) of different grades and origins was determined. The ER can provide a theoretical basis for distinguishing Longjing tea of different grades and origins, and for identifying the authenticity of Longjing tea. The ER ratio of (R)-(-)-1-octen-3-ol and (S)-(+)-1-octen-3-ol can be used to identify LG1 (71:29). The ER ratio of (S)-(+)-α-ionone and (R)-(-)-α-ionone can be used to identify LG2 (65:35). The ER ratio of (R)-(-)-Dihydroactinidiolide to (S)-(+)-Dihydroactinidiolide (71:29) can also be used to detect LG3. The ER ratio of (R)-(+)-Limonene and (S)-(-)-limonene can be used to identify LG4 (20:80). The ER ratio of (R)-(-)-linalool to (S)-(+)-linalool (12:83) was available to identify LG5.
Supercritical CO2 Extraction of Narcissus poeticus L. Flowers for the Isolation of Volatile Fragrance Compounds
Molecules 2022 Jan 6;27(2):353.PMID:35056665DOI:10.3390/molecules27020353.
The flowers of Narcissus poeticus are used for the isolation of valuable fragrance substances. So far, as the majority of these substances consist of volatile and sensitive to heat compounds, there is a need of developing effective methods for their recovery. In this study, freeze-dried N. poeticus inflorescences were extracted with pure supercritical CO2 (SFE-CO2) and its mixture with 5% co-solvent ethanol (EtOH) at 40 °C. Extract yields varied from 1.63% (12 MPa) to 3.12% (48 MPa, 5% EtOH). In total, 116 volatile compounds were identified by GC-TOF/MS in the extracts, which were divided into 20 different groups. Benzyl benzoate (9.44-10.22%), benzyl linoleate (1.72-2.17%) and benzyl alcohol (0.18-1.00%) were the major volatiles among aromatic compounds. The amount of the recovered benzyl benzoate in N. poeticus SFE-CO2 extracts varied from 58.98 ± 2.61 (24 MPa) to 91.52 ± 1.36 (48 MPa) mg/kg plant dry weight (pdw). α-Terpineol dominated among oxygenated monoterpenes (1.08-3.42%); its yield was from 9.25 ± 0.63 (12 MPa) to 29.88 ± 1.25 (48 MPa/EtOH) mg/kg pdw. Limonene was the major monoterpene hydrocarbon; (3E)-hexenol and heneicosanol dominated among alcohols and phenols; dihydroactinidiolide and 4,8,12,16-tetramethyl heptadecan-4-olide were the most abundant lactones; heptanal, nonanal, (2E,4E)-decadienal and octadecanal were the most abundant aldehydes. The most important prenol lipids were triterpenoid squalene, from 0.86 ± 0.10 (24 MPa) to 7.73 ± 0.18 (48 MPa/EtOH) mg/kg pdw and D-α-tocopherol, from 1.20 ± 0.04 (12 MPa) to 15.39 ± 0.31 (48 MPa/EtOH) mg/kg pdw. Aliphatic hydrocarbons (waxes) constituted the main part (41.47 to 54.93%) in the extracts; while in case of a 5% EtOH the percentage of alkanes was the lowest. The fraction of waxes may be removed for the separation of higher value fragrance materials. In general, the results obtained are promising for a wider application of SFE-CO2 for the recovery of fragrance substances from N. poeticus flowers.
Cytotoxicity, genotoxicity, and gene expression changes induced by methanolic extract of Moringa stenopetala leaf with LC-qTOF-MS metabolic profile
Toxicon 2021 Nov;203:40-50.PMID:34610271DOI:10.1016/j.toxicon.2021.09.025.
Moringa stenopetala (Baker f.) Cuf.and other Moringa species have traditionally been used to treat various diseases. The purpose of this study was to determine the cytotoxic and genotoxic effects of the methanolic extract of M. stenopetala leaf and its fractions on selected tumor cells. Cytotoxicity was determined by MTT assay. The comet assay was used toassess DNA damage, and gel electrophoresis was used to determine DNA fragmentation. Gene expression was analyzed by qPCR using two specific genes for each cancer cell line. Fractionation of the methanolic extract (E-1) on Diaion HP-20 yielded five fractions (Fr-2 to Fr-6); only Fr-4 and Fr-6 were cytotoxic to breast cancer cells (MCF-7; IC50 = 58.3 ± 0.93 and 35.8 ± 2.44 μg/mL, respectively), human hepatocellular carcinoma cells (HepG2; IC50 = 57.8 ± 1.57 and 39.3 ± 1.90 μg/mL, respectively), and Fr-4 was cytotoxic to human colon cancer cells (HCT-116; IC50 = 94.2 ± 4.9 μg/mL). In addition, exposure of the cancer cells to Fr-4 and Fr-6 resulted in a high level of DNA damage. Moreover, relative expression of MTAP and CDKN2A in MCF-7 were increased, whereas expression of p21 and p53 in HCT-116, and APC and TERT in HepG2 were decreased, similar to that of doxorubicin. LC-qTOF-MS was used to identify metabolites in E-1, the majority of which were enriched in Fr-4. Two terpenes (loliolide and dihydroactinidiolide), the majority of the flavonoids, and niazirin were about two fold enriched in Fr-4, whereas the majority of the lipids were 4-10 fold enriched. However, Fr-6 hardly showed compounds other than the two terpenes that were enriched 1.5 and 7 fold. The findings suggest that Fr-4 and Fr-6 are promising sources of compounds possessing cytotoxic and genotoxic properties.