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(-)-Epiafzelechin

$1,400 $1,260

  • Brand : BIOFRON

  • Catalogue Number : BN-O1348

  • Specification : 98%(HPLC)

  • CAS number : 24808-04-6

  • Formula : C15H14O5

  • Molecular Weight : 274.27

  • PUBCHEM ID : 443639

  • Volume : 5MG

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Catalogue Number

BN-O1348

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

274.27

Appearance

Powder

Botanical Source

Mangosteen

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O

Synonyms

(2R,3R)-2-(4-Hydroxyphenyl)-3,5,7-chromanetriol/(-)-epiafzelechin/2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3R)-/Afzelechin/(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol/ent-epiafzelechin/epi-Afzelechin/3,5,7,4'-Tetrahydroxyflavan

IUPAC Name

(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

Applications

Density

1.5±0.1 g/cm3

Solubility

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

Flash Point

306.6±30.1 °C

Boiling Point

583.4±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

InChl Key

RSYUFYQTACJFML-UKRRQHHQSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:24808-04-6) 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

28531166

Abstract

The present study was designed to characterize the bone protective effects of (-)-epiafzelechin (EAF), a flavan-3-ol, in mature ovariectomized mice model and its ability to stimulate osteoblastic activity and inhibit osteoclastic activity. Mature C57BL/6 mice (three to four months old) were either ovariectomised (OVX) or sham-operated and subjected to treatment (vehicle, 17β-oestradiol (E2, 200 μg/kg/day) or EAF (500 μg/kg/day) orally for six weeks. EAF and E2 significantly reduced urinary calcium (Ca) excretion, serum osteocalcin (OCN), and urinary deoxy-pyridinoline (DPD); increased bone mineral density (BMD); and improved micro-architectural properties in OVX mice. EAF significantly increased cell viability, alkaline phosphatise (ALP) activity, and collagen content, as well as runt-related transcriptional factor 2 (Runx2) mRNA expression in murine osteoblastic MC3T3-E1 cells. In addition, EAF significantly reduced the viability of osteoclast precursor murine leukemia monocyte RAW 264.7 cells and tartrate-resistant acid phosphatase (TRAP) activities in mature osteoclastic RAW 264.7 cells. EAF is a bioactive flavan-3-ol that protects estrogen deficiency-induced bone loss in OVX mice and exerts direct modulating effects in bone cells in vitro.

KEYWORDS

(−)-epiafzelechin; flavan-3-ol; osteoclastogenesis; osteogenesis; ovariectomised; trabecular bone

Title

(-)-Epiafzelechin Protects against Ovariectomy-induced Bone Loss in Adult Mice and Modulate Osteoblastic and Osteoclastic Functions In Vitro.

Author

Wong KC1,2, Cao S3,4, Dong X5,6, Law MC7, Chan TH8,9, Wong MS10,11,12.

Publish date

2017 May 22

PMID

25108364

Abstract

(-)-Epiafzelechin is a flavan-3-ol commonly found in plant source. Biological studies suggested that (-)-epiafzelechin may have anti-inflammatory, anti-oxidant and bone-protective effect. However, it’s in vivo efficacy remains to be demonstrated. A specific detection method for (-)-epiafzelechin was successfully developed by using UPLC-MS/MS to quantify the amount of (-)-epiafzelechin present in mice plasma after a liquid-liquid extraction by ethyl acetate. The separation was achieved by using a reversed-phase C18 column with a 16 min gradient elution protocol consisting of water (0.1%, v/v, formic acid) and 0-70% ACN (0.1%, v/v, formic acid). The lower limit of quantitation for (-)-epiafzelechin was found to be 12.5 ng/mL. This method exhibited a good linearity (r(2)=0.992). The intra-day and inter-day precision were within 12%, while the accuracy was between 97.6 and 113. 4%. A quantity of 10mg/kg synthetic (-)-epiafzelechin was administered to C57BL/6J mice by intravenous (i.v.) and intraperitoneal (i.p.) injections and the blood was collected at different time points. The plasma was then analyzed by the UPLC-MS/MS method, and the plasma drug concentration-time curves for i.v. and i.p. (-)-epiafzelechin injection were constructed. The maximum concentrations (Cmax) of (-)-epiafzelechin in blood by i.v. and i.p. injection were found to be 10.6 and 6.0 μg/mL, respectively, while the time for reaching Cmax in i.p. injection was found to be 15 min. The distribution half-lives of (-)-epiafzelechin after i.v. and i.p. injection were found to be 7.0 and 12.6 min, respectively. Some of the PK parameters were found to be similar in both i.v. and i.p. injections of (-)-epiafzelechin owing to its high solubility in water.

Copyright © 2014 Elsevier B.V. All rights reserved

KEYWORDS

(−)-Epiafzelechin; Intraperitoneal; Intravenous; Pharmacokinetics; UPLC-MS/MS

Title

Development of a UPLC-MS/MS bioanalytical method for the pharmacokinetic study of (-)-epiafzelechin, a flavan-3-ol with osteoprotective activity, in C57BL/6J mice.

Author

Wong KC1, Law MC1, Wong MS2, Chan TH3.

Publish date

2014 Sep 15

PMID

10418338

Abstract

An inhibitor of cyclooxygenase (COX)-1 activity of prostaglandin H2 synthase was isolated from aerial parts of Celastrus orbiculatus Thunb. (Celastraceae), an oriental folk medicine for rheumatoid arthritis by activity-guided column chromatographic methods. The COX inhibitor was identified as (-)-epiafzelechin, a member of flavan-3-ols by the structural analysis with HR-EI-mass, 1H-NMR and 13C-NMR spectral data. The compound exhibited a dose-dependent inhibition on the COX activity with an IC50 value of 15 microM. (-)-Epiafzelechin exhibited about 3-fold weaker inhibitory potency on the enzyme activity than indomethacin as a positive control. (-)-Epiafzelechin exhibited significant anti-inflammatory activity on carrageenin-induced mouse paw edema when the compound (100 mg/kg) was orally administrated at 1 h before carrageenin treatment.

Title

(-)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus.

Author

Min KR, Hwang BY, Lim HS, Kang BS, Oh GJ, Lee J, Kang SH, Lee KS, Ro JS, Kim Y.

Publish date

1999 Jun