Apiole

Apiole
Names
	Preferred IUPAC name 4,7-Dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
	Other names 5-Allyl-4,7-dimethoxybenzo[d][1,3]dioxole; 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene
Identifiers
CAS Number	523-80-8 [clarification needed] ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:70353;
ChEMBL	ChEMBL1560118 ;
ChemSpider	21106259 ;
ECHA InfoCard	100.007.592
EC Number	208-349-2;
KEGG	C10429 ;
PubChem CID	10659;
UNII	QQ67504PXO ;
CompTox Dashboard (EPA)	DTXSID4041236 ;
	InChI InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3 Key: QQRSPHJOOXUALR-UHFFFAOYSA-N ; InChI=1/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3 Key: QQRSPHJOOXUALR-UHFFFAOYAO;
	SMILES COc1cc(CC=C)c(OC)c2OCOc12;
Properties
Chemical formula	C12H14O4
Molar mass	222.23 g/mol
Density	1.151 g/mL
Melting point	30 °C (86 °F; 303 K)
Boiling point	294 °C (561 °F; 567 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Apiole is a

amenorrea or lack of menstruation

.

In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders and as an abortifacient. It is an irritant and, in high doses, it can cause liver and kidney damage.[3] Cases of death due to attempted abortion using apiole have been reported.^[4]^[5]

Hippocrates wrote about parsley as an herb to cause an abortion.^[6] Plants containing apiole were used by women in the Middle Ages to terminate pregnancies. Now that safer methods of abortion are available, apiol is almost forgotten.

Orthography

Apiole (always with the final 'e') is the correct spelling^[

Jamaican ginger) was introduced on the American market. 1'-sulfoxy metabolite formation for apiole (3,4-OMe-safrole) is about 1/3 as active as safrole.^[8] No carcinogenicity was detected with parsley apiol or dill apiol in mice.^[9]

Other similarly named compounds

The name apiole is also used for a closely related compound found in dill and in fennel roots, the positional isomer (dillapiole, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene. Exalatacin (1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene) is another positional isomer of apiole, found in the Australian plants Crowea exalata and Crowea angustifolia var. angustifolia.^{[citation needed]}

See also

Dillapiole

Myristicin

References

ISBN 9781845934057
.

^ Shorter, Edward (1991). Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine. New Brunswick, NJ: Transaction Publishers.^{[page needed]}

PMID 5736450
.

PMID 20325694
.

PMID 13320936
.

ISBN 978-0-9645920-0-1.^{[page needed}
]

S2CID 4189608.^{[failed verification}
]

PMID 26826679
.

PMID 6499112
.

External links

Apiol chemical information from chemindustry.com^{[permanent dead link]}

v
t
e
Types of phenylpropenes
Phenylpropenes

Anethole

Apiole

Asaricin

Asarone

Carpacin

Chavibetol

Chavicol

Croweacin

Dillapiole

Elemicin

Estragole

Eugenol

Exalatacin

Isoapiole

Isodillapiole

Isoeugenol

Isomyristicin

Isosafrole

Methyl eugenol

Methyl isoeugenol

Myristicin

Nothoapiole

Osmorhizole

Pseudoisoeugenol

Safrole

Retrieved from "https://en.wikipedia.org/w/index.php?title=Apiole&oldid=1192625374"

[1] ISBN 9781845934057
.

[2] Shorter, Edward (1991). Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine. New Brunswick, NJ: Transaction Publishers.^{[page needed]}

[3] PMID 5736450
.

[4] PMID 20325694
.

[5] PMID 13320936
.

[6] ISBN 978-0-9645920-0-1.^{[page needed}
]

[7] S2CID 4189608.^{[failed verification}
]

[8] PMID 26826679
.

[9] PMID 6499112
.

[4]

[5]

[6]

[8]

[9]