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Guaiazulene

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-G3001

  • Specification : 98%

  • CAS number : 489-84-9

  • Formula : C15H18

  • Molecular Weight : 198.3

  • Volume : 50mg

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Catalogue Number

BF-G3001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

198.3

Appearance

Powder

Botanical Source

Aglaia odorata

Structure Type

Terpenoids

Category

SMILES

CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C

Synonyms

IUPAC Name

Density

0.976

Solubility

DMSO : 250 mg/mL (1260.72 mM; Need ultrasonic)

Flash Point

142.3±13.1 °C

Boiling Point

305.4±22.0 °C at 760 mmHg

Melting Point

27-29 °C(lit.)

InChl

InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

InChl Key

FWKQNCXZGNBPFD-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2902190000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:489-84-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29695558

Abstract

Background/aim: Guaiazulene (1,4-dimethyl-7-isopropylazulene) is present in several essential oils of medicinal and aromatic plants. There exist few studies that investigated the anticancer activity of guaiazulenes. We investigated the relative cytotoxicity of 10 alkylaminoguaiazulene derivatives towards both cancer and normal cells.

Materials and methods: Cytotoxicity towards four human oral squamous cell carcinoma (OSCC) cell lines and five types of human normal oral cells (gingival fibroblasts, periodontal ligament fibroblasts, pulp cells and keratinocytes, gingival epithelial progenitors) was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Tumor specificity (TS) was evaluated as the ratio of the mean 50% cytotoxic concentration against normal oral cells to that against OSCC cell lines. Apoptosis-inducing activity was evaluated by cleavage of poly ADP-ribose polymerase and caspsase-3 with western blot analysis.

Results: Validity of the present TS measurement method was confirmed using methotrexate. With increasing length of the alkyl group of alkylaminoguaiazulene derivatives, cytotoxicity increased. Introduction of oxygen, nitrogen or sulfur atom into the alkyl group slightly reduced cytotoxicity. Most compounds had very low TS, no synergistic action with methotrexate and doxorubicin, nor did they induce apoptosis of OSCC cells. On the other hand, compound [10], containing a morpholino group, induced apoptosis of OSCC cells.

Conclusion: The cytotoxicity of alkylaminoguaiazulenes is not always coupled with TS and apoptosis-inducing activity.

KEYWORDS

Alkylaminoguaiazulene; alkylation; apoptosis; cytotoxicity; morpholine backbone; tumor specificity.

Title

In Vitro Antitumor Activity of Alkylaminoguaiazulenes

Author

Mari Uehara 1, Himawari Minemura 1, Tsunenori Ohno 1, Masashi Hashimoto 1, Hidetsugu Wakabayashi 2, Noriyuki Okudaira 3, Hiroshi Sakagami 4

Publish date

May-Jun 2018;

PMID

26757553

Abstract

Seven guaiane-type sesquiterpenoids, a new compound 6-formyl-5-isopropyl-3-hydroxymethyl-7-methyl-1H-indene (1), a new natural product 5-isopropyl-3, 7-dimethyl-1H-indene-1-one (2), along with five known compounds: guaiazulene (3), 4-formyl-7-isopropyl-10-methylazulene (4), sesquiterpene ketolactone (5), alismoxide (6) and guaia-1 (5), 6-diene (7), were isolated from gorgonian Muriceides collaris collected in South China Sea. Their structures were elucidated on the basis of extensive spectroscopic analysis [MS, IR, 1H NMR, 13C NMR (DEPT), HMQC, HMBC, NOESY] and by comparison of the spectral data with those of the literatures.

Title

[Sesquiterpenoids from gorgonian Muriceides collaris]

Author

Xue-feng Shi, Wei-hong He, Guo-qiang Li

Publish date

2015 Sep

PMID

24637960

Abstract

Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3-6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configuration of 1 was determined as 3R by the comparison of TDDFT calculated electronic circular dichroism with its experimental spectrum. Compound 1 is a rare guaiazulene-based analogue possessing a unique C₁₆ skeleton. The possible generation process of 1 through an intermolecular one-carbon-transfer reaction was also discussed. Compound 2 was previously described as a presumed intermediate involved in the biogenesis of anthogorgienes A and I. Compound 3 exhibited antiproliferative effects on the embryo development of zebrafish Danio rerio.

Title

Ochracenoids A and B, guaiazulene-based analogues from gorgonian Anthogorgia ochracea collected from the South China Sea

Author

Juan-Juan Zheng 1, Chang-Lun Shao 2, Min Chen 3, Li-She Gan 4, Yu-Chun Fang 5, Xu-Hui Wang 6, Chang-Yun Wang 7

Publish date

2014 Mar 14;


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