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β-Eleostearic acid

Names

[ CAS No. ]:
506-23-0

[ Name ]:
β-Eleostearic acid

[Synonym ]:
9Z,11E,13E-Octadecatrienoic Acid
9,11,13-Octadecatrienoic acid, (E,E,E)-
(9E,11E,13E)-Octadeca-9,11,13-trienoic acid
(E,E,E)-9,11,13-octadecatrienoic acid
9(Z),11(E),13(E)-OCTADECATRIENOIC ACID
α-Eleostearic acid
(9Z,11E,13E)-9,11,13-Octadecatrienoic acid
(9Z,11E,13E)-octadeca-9,11,13-trienoic acid
cis-9, trans-11, trans-13-octadecatrienoic acid
9-cis,11-trans,13-trans-octadecatrienoic acid
(9E,11E,13E)-9,11,13-Octadecatrienoic acid
(E,E,E)-octadeca-9,11,13-trienoic acid
9,11,13-Octadecatrienoic acid, (9E,11E,13E)-
β-Eleostearic acid
9E,11E,13E-octadecatrienoic acid
a-Eleostearic Acid
9,11,13-Octadecatrienoic acid, (9Z,11E,13E)-
(9Z,11E,13E)-Octadecatrienoic acid
trans-9, trans-11, trans-13-octadecatrienoic acid

Biological Activity

[Description]:

α-Eleostearic acid (cis-Eleostearic acid), a conjugated linolenic acid, is an apoptosis inducer. α-Eleostearic acid is also a ferroptosis inducer. α-Eleostearic acid exhibits antioxidant and antitumor activity[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Apoptosis >> Ferroptosis
Research Areas >> Metabolic Disease

[In Vitro]

α-Eleostearic acid (0-40 μM; 24 h) 抑制一些癌细胞系和成纤维细胞系的生长，包括 HL60 细胞和 HT29 细胞[1]。 α-Eleostearic acid (20 μM; 6 h) 在 HL60 细胞中诱导典型的细胞凋亡现象：细胞和核碎裂，以及核小体 DNA 碎裂[1]。 α-Eleostearic acid (0.01-100 μM; 72 h) 触发 MDA-MB-231 细胞死亡，这种死亡被 Fer-1、Deferoxamine 和维生素 E 抑制[1]。

[In Vivo]

α-Eleostearic acid (0.5% of total lipid given; p.o.) 抑制 Sodium Arsenite 诱导的体内氧化应激：逆转抗氧化酶活性和降低脂质过氧化水平[2]。 在侵袭性 TNBC 原位异种移植模型中，给小鼠口服天然富含 α-Eleostearic acid 的桐油可限制肿瘤生长和转移[3]。

[References]

[1]. Kobori M, et, al. Alpha-eleostearic acid and its dihydroxy derivative are major apoptosis-inducing components of bitter gourd. J Agric Food Chem. 2008 Nov 26;56(22):10515-20.  

[2]. Saha SS, et, al. Comparative study of antioxidant activity of alpha-eleostearic acid and punicic acid against oxidative stress generated by sodium arsenite. Food Chem Toxicol. 2009 Oct;47(10):2551-6.  

[3]. Beatty A, et, al. Ferroptotic cell death triggered by conjugated linolenic acids is mediated by ACSL1. Nat Commun. 2021 Apr 14;12(1):2244.  

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
390.6±11.0 °C at 760 mmHg

[ Molecular Formula ]:
C18H30O2

[ Molecular Weight ]:
278.430

[ Flash Point ]:
287.4±14.4 °C

[ Exact Mass ]:
278.224579

[ PSA ]:
37.30000

[ LogP ]:
6.66

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.491

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds