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Bisabolol oxide A

$672

  • Brand : BIOFRON

  • Catalogue Number : BD-D1260

  • Specification : 98%(HPLC)

  • CAS number : 22567-36-8

  • Formula : C15H26O2

  • Molecular Weight : 238.37

  • PUBCHEM ID : 13092559

  • Volume : 25MG

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Catalogue Number

BD-D1260

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

238.37

Appearance

Powder

Botanical Source

Structure Type

Monoterpenoids

Category

SMILES

CC1=CCC(CC1)C2(CCC(C(O2)(C)C)O)C

Synonyms

(3S,6S)-2,2,6-trimethyl-6-[(1S)-4-methylcyclohex-3-en-1-yl]oxan-3-ol

IUPAC Name

(3S,6S)-2,2,6-trimethyl-6-[(1S)-4-methylcyclohex-3-en-1-yl]oxan-3-ol

Applications

Density

0.982 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

125.9ºC

Boiling Point

327.7ºC at 760 mmHg

Melting Point

InChl

InChI=1S/C15H26O2/c1-11-5-7-12(8-6-11)15(4)10-9-13(16)14(2,3)17-15/h5,12-13,16H,6-10H2,1-4H3/t12-,13+,15+/m1/s1

InChl Key

WJHRAVIQWFQMKF-IPYPFGDCSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:22567-36-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

24070008

Abstract

German chamomile (Matricaria chamomilla) is one of the most popular medicinal plants used in Western herbal medicine. Among the various phytochemicals present in the essential oil of the flowers of German chamomile, bisabolol and its oxidized metabolites are considered as marker compounds for distinguishing different chemotypes. These compounds are influential in mediating the aroma of the essential oil of M. chamomilla and contribute to the therapeutic properties (anti-inflammatory, antibacterial, insecticidal, and antiulcer) of this species. In order to find other possible bisabolol derivatives as marker compounds for authentication of German chamomile in botanical and commercial products, an in-depth investigation using a GC-assisted fractionation procedure was performed on nonpolar fractions. As a result of this approach, three new hydroxylated derivatives of bisabolol oxides A and B (1-3) have been isolated from M. chamomilla. Plausible biogenetic pathways are presented.

Title

Hydroxylated bisabolol oxides: evidence for secondary oxidative metabolism in Matricaria chamomilla

Author

Cristina Avonto 1, Mei Wang, Amar G Chittiboyina, Bharathi Avula, Jianping Zhao, Ikhlas A Khan

Publish date

2013 Oct 25;

PMID

23873581

Abstract

Bisabololoxide A (BSBO), main constituents in German chamomile extract, is responsible for antipruritic effect. In previous study, the incubation with 30-100 μM BSBO for 24 h exerted cytotoxic and proapoptotic effects on rat thymocytes. To further characterize BSBO cytotoxicity, the effect on the cells suffering from calcium overload by calcium ionophore A23187 was examined. A23187 induced Ca(2+) -dependent cell death. Contrary to our expectation, 1-10 μM BSBO inhibited A23187-induced increase in cell lethality of rat thymocytes. BSBO attenuated A23187-induced increases in populations of shrunken living cells, phosphatidylserine-exposed living cells, and dead cells, without affecting the increase in intracellular Ca(2+) concentration and the Ca(2+) -dependent hyperpolarization. The effect of BSBO on A23187-treated cells may be unique because the activation of Ca(2+) -dependent K(+) channels is required for cell shrinkage, externalization of phosphatidylserine, and cell death in some cells. The cell death induced by A23187 was not inhibited by Z-VAD-FMK, a pan-inhibitor of caspases. Thus, the cell death may be a necrosis with some features observed during an early stage of apoptosis. These results suggest that BSBO at low micromolar concentrations is cytoprotective against calcium overload.

KEYWORDS

bisabololoxide A; calcium overload; cell death; chamomile extract.

Title

Bisabololoxide A, one of the constituents in German chamomile extract, attenuates cell death induced by calcium overload

Author

Eri Fukunaga 1, Yumi Hirao, Ikuko Ogata-Ikeda, Yumiko Nishimura, Hakaru Seo, Yasuo Oyama

Publish date

2014 May;

PMID

20863677

Abstract

German chamomile (Matricaria recutita L.) is a popular ingredient in herbal teas. In previous study, micromolar bisabololoxide A, one of main constituents in German chamomile, exerted cytotoxic action on rat thymocyte, a normal non-proliferative cell. This result prompted us to study the effect of bisabololoxide A on proliferative cancer cells and to seek the possibility of its use with 5-fluorouracil, an anticancer agent. In this study, the effect of micromolar bisabololoxide A on human leukemia K562 cells was cytometrically examined. Although the incubation of K562 cells with 10 μM bisabololoxide A for 72h did not significantly increase the percentage populations of dead cells and shrunken cells, the inhibitory action on the growth was obviously observed. It was not the case for the concentrations of less than 5 μM. The threshold concentration of bisabololoxide A to exert the cytotoxic action on K562 cells was ascertained to be 5-10 μM. Bisabololoxide A at 5-10 μM did not exert cytotoxic action on normal non-proliferative cells (rat thymocytes) in our previous study. Since the antiproliferative action of micromolar bisabololoxide A on cancerous cells was expected to be beneficial to cancer treatment, the modification of antiproliferative action of 5-fluorouracil (3-30 μM) by bisabololoxide A was studied. The combination of 5-fluorouracil and bisabololoxide further inhibited the growth of K562 cells although the additive inhibition of growth by bisabololoxide A became smaller as the concentration of 5-fluorouracil increased. Therefore, it is suggested that the simultaneous application of German chamomile containing bisabololoxide A may reduce the dose of 5-fluorouracil.

Title

Cytotoxic action of bisabololoxide A of German chamomile on human leukemia K562 cells in combination with 5-fluorouracil

Author

Ikuko Ogata-Ikeda 1, Hakaru Seo, Takuya Kawanai, Erika Hashimoto, Yasuo Oyama

Publish date

2011 Mar 15;