Erythrodiol Chemical Properties

Melting point:

230-231 °C(lit.)

Boiling point:

520.5±50.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly, Sonicated), Methanol (Slightly)

pka

15.09±0.10(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

insoluble in water

BRN 

2340203

InChIKey

PSZDOEIIIJFCFE-MMIPUHLFNA-N

SMILES

[C@@]12(C)CC[C@@]3(CO)CCC(C)(C)C[C@@]3([H])C1=CC[C@]1([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]21C |&1:0,4,13,18,20,24,29,33,r|

LogP

9.180 (est)

CAS DataBase Reference

545-48-2(CAS DataBase Reference)

Safety Information

Risk Statements 

22

Safety Statements 

2-45

WGK Germany 

3

F 

10-23

MSDS

• Language:English Provider:SigmaAldrich

Erythrodiol Usage And Synthesis

Description

Erythrodiol is a triterpene that has been found in olive oil and has diverse biological activities. It induces relaxation of isolated rat aortic rings precontracted with phenylephrine (EC₅₀ = 3.38 μM). Erythrodiol inhibits the growth of HT-29 adenocarcinoma cells (EC₅₀ = 48.8 μM). It induces production of reactive oxygen species (ROS) and apoptosis in MCF-7 cells when used at a concentration of 100 μM. Topical administration of erythrodiol (0.5 mg/ear) reduces ear edema and myeloperoxidase (MPO) activity induced by phorbol 12-myristate 13-acetate (TPA; ) in mice.

Uses

It is an essential reagent in the synthesis of aminopropoxytriterpenoids that have anticancer activity. 3β-Erythrodiol has pharmacological property as a vasodilatory agent. It may have interesting therapeutic potential as a new vasodilator drug, for protecting the cardiovascular system.

Definition

ChEBI: Erythrodiol is a pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a primary alcohol, a secondary alcohol and a diol. It is functionally related to a beta-amyrin.

References

[1] ROSALíA RODRíGUEZ-RODRíGUEZ. Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in “orujo” olive oil, on rat aorta.[J]. British Journal of Nutrition, 2004, 92 4: 635-642. DOI: 10.1079/bjn20041231
[2] M. EMíLIA JUAN. Erythrodiol, a natural triterpenoid from olives, has antiproliferative and apoptotic activity in HT-29 human adenocarcinoma cells[J]. Molecular Nutrition & Food Research, 2008, 52 5: 595-599. DOI: 10.1002/mnfr.200700300
[3] YOSRA ALLOUCHE. Antioxidant, Antiproliferative, and Pro-apoptotic Capacities of Pentacyclic Triterpenes Found in the Skin of Olives on MCF-7 Human Breast Cancer Cells and Their Effects on DNA Damage[J]. Journal of Agricultural and Food Chemistry, 2010, 59 1: 121-130. DOI: 10.1021/jf102319y
[4] SALVADOR Má?EZ. Effect of selected triterpenoids on chronic dermal inflammation[J]. European journal of pharmacology, 1997, 334 1: Pages 103-105. DOI: 10.1016/s0014-2999(97)01187-4

Erythrodiol(545-48-2)Related Product Information

• Estradiol
• Ethylene glycol
• Propylene glycol
• Oleanolic acid
• Androstenediol
• Polyethylene Glycol
• Maslinic acid
• CAULOPHYLLOGENIN
• Methyl oleanolate
• Hederagenin
• Hederacoside C
• esculentoside E
• Ethyl (3beta)-3-hydroxyolean-12-en-28-oate
• ECHINOCYSTIC ACID-3-GLUCOSIDE
• araloside A
• GinsenosideRo
• ECHINOCYSTIC ACID
• ALPHA-HEDERIN