Abietic acid

Abietic acid
Names
	IUPAC name Abieta-7,13-dien-18-oic acid
	Systematic IUPAC name (1R,4aR,4bR,10aR)-1,4a-Dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid
	Other names Abietinic acid; Sylvic acid
Identifiers
CAS Number	514-10-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28987 ;
ChEMBL	ChEMBL71893 ;
ChemSpider	10127 ;
ECHA InfoCard	100.007.436
EC Number	208-173-3;
KEGG	C06087 ;
PubChem CID	10569;
RTECS number	TP8580000;
UNII	V3DHX33184 ;
CompTox Dashboard (EPA)	DTXSID7022047 ;
	InChI InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1 Key: RSWGJHLUYNHPMX-ONCXSQPRSA-N ; InChI=1/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1 Key: RSWGJHLUYNHPMX-ONCXSQPRBK;
	SMILES O=C(O)[C@]3([C@@H]2C/C=C1/C=C(\CC[C@@H]1[C@@]2(C)CCC3)C(C)C)C;
Properties
Chemical formula	C20H30O2
Molar mass	302.458 g·mol−1
Appearance	Yellow resinous powder, crystals or chunks. Monoclinic plates (from EtOH/water). Colorless solid when pure.
Density	1.06 g/mL
Melting point	172–175 °C (342–347 °F; 445–448 K)
Boiling point	250 °C; 482 °F; 523 K
Solubility in water	Insoluble
Solubility in other solvents	Very soluble in acetone, petroleum ether, Et2O, and ethanol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)	1 0 0
Safety data sheet (SDS)	MSDS
	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

Abietic acid (also known as abietinic acid or sylvic acid) is a diterpenoid found in coniferous trees. It is supposed to exist as a defend the host plant from insect attack or various wounds. Chemically, it is a complicated molecule featuring two alkene groups and a carboxylic acid within a chiral tricyclic framework. As the major component of rosin, it is a commercially important. Historically speaking, it was a major component of naval stores. It is the most common of the resin acids. Another common resin acid is pimaric acid, which converts to abietic acid upon heating.

Characteristics

Abietic acid is found in rosin obtained from pine trees.^[3] Pure abietic acid is a colorless solid, but commercial samples are usually a glassy or partly crystalline yellowish solid that melts at temperatures as low as 85 °C (185 °F).^[4] Abietic acid is soluble in alcohols, acetone, and ethers. Its esters and salts are called an abietates, e.g. ethyl abietate and sodium abietate.^[5]

Biosynthesis

Route from copalyl pyrophosphate to abietadiene , precursor to abietic acid (PP = pyrophosphate).

Abietic acid is derived from the diterpene abietadiene, which in turn is made from copalyl pyrophosphate, which is derived from geranylgeranyl pyrophosphate, the precursor to many diterpenoids. In air and in the presence of certain cytochrome P450 enzymes, abietadiene is oxidized to abietic acid. An entire family of so-called resin acids form similarly. Together with abietic acid, these resin acids are a major portion of rosin, the solid portion of the oleoresin of coniferous trees.

Preparation

Abietic acid is extracted from tree rosin. Laboratory procedures illustrate the nature of the extraction, which is the basic of a large industry.^[6]

Uses

As a component of rosin and one of the principal resin acid]]s, abietic acid has many uses, e.g. in some paints, soaps, foods, soldering flux,

Safety

As the chief component of rosin, abietic acid is approved by the US FDA as a miscellaneous food additive.^[7]
Abietic acid is considered a "nonhazardous natural substance" in tall oil ("liquid rosin").^[5]
In the U.S., abietic acid is listed in the inventory of the Toxic Substances Control Act.
Abietic acid is the primary irritant in pine wood and resin. As a contact allergen^[8] it is the cause of abietic acid dermatitis. (However, compounds resulting from its oxidation by air elicit stronger responses.) ^[9]
50% ethanol extracts from Resina pini of Pinus sp. (Pinaceae) showed inhibitory activity against testosterone 5α-reductase prepared from rat prostate. The fraction responsible for this activity was purified, and the active constituent was isolated and identified as abietic acid, which exhibited potent inhibitory activity against testosterone 5α-reductase in vitro.^[10]

References

^ National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina
^ ^a ^b Merck Index, 12th Edition, 3. Abietic Acid
^ "Abietic Acid". Dr. Duke's Phytochemical and Ethnobotanical Databases. Archived from the original on 2015-09-23. Retrieved 13 January 2012.
^ Hoiberg, Dale H., ed. (2010). "abietic acid". Encyclopædia Britannica. Vol. I: A-ak Bayes (15th ed.). Chicago, Illinois: Encyclopædia Britannica Inc. pp. 32. ISBN 978-1-59339-837-8.
^ ^a ^b Lars-Hugo Norlin "Tall Oil" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a26_057
^ G. C. Harris and T. F. Sanderson (1963). "Abietic Acid". Organic Syntheses. 32: 1. doi:10.15227/orgsyn.032.0001.
^ Nutrition, Center for Food Safety and Applied (2022-08-25). "Food Additive Status List". FDA.
^ El Sayed, F; Manzur, F; Bayle, P; Marguery, MS; Bazex, J (1995). "Contact urticaria from abietic acid". Contact Dermatitis. 32 (6): 361–2. doi:10.1111/j.1600-0536.1995.tb00628.x. PMID 7554886. S2CID 36139468.
^ Hausen, BM; Krohn, K; Budianto, E (1990). "Contact allergy due to colophony (VII). Sensitizing studies with oxidation products of abietic and related acids". Contact Dermatitis. 23 (5): 352–8. doi:10.1111/j.1600-0536.1990.tb05171.x. PMID 2096024. S2CID 34726630.
^ Seong-Soo Roh, Moon-Ki Park and Yong-ung Kim (2010). "Abietic Acid from Resina Pini of Pinus Species as a Testosterone 5α-Reductase Inhibitor". J. Health Sci. 56 (4): 451–455. doi:10.1248/jhs.56.451.

External links

[1] National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina

[Merck-2] Merck Index, 12th Edition, 3. Abietic Acid

[3] "Abietic Acid". Dr. Duke's Phytochemical and Ethnobotanical Databases. Archived from the original on 2015-09-23. Retrieved 13 January 2012.

[EB-4] Hoiberg, Dale H., ed. (2010). "abietic acid". Encyclopædia Britannica. Vol. I: A-ak Bayes (15th ed.). Chicago, Illinois: Encyclopædia Britannica Inc. pp. 32. ISBN 978-1-59339-837-8.

[tall-5] Lars-Hugo Norlin "Tall Oil" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a26_057

[6] G. C. Harris and T. F. Sanderson (1963). "Abietic Acid". Organic Syntheses. 32: 1. doi:10.15227/orgsyn.032.0001.

[:0-7] Nutrition, Center for Food Safety and Applied (2022-08-25). "Food Additive Status List". FDA.

[8] El Sayed, F; Manzur, F; Bayle, P; Marguery, MS; Bazex, J (1995). "Contact urticaria from abietic acid". Contact Dermatitis. 32 (6): 361–2. doi:10.1111/j.1600-0536.1995.tb00628.x. PMID 7554886. S2CID 36139468.

[9] Hausen, BM; Krohn, K; Budianto, E (1990). "Contact allergy due to colophony (VII). Sensitizing studies with oxidation products of abietic and related acids". Contact Dermatitis. 23 (5): 352–8. doi:10.1111/j.1600-0536.1990.tb05171.x. PMID 2096024. S2CID 34726630.

[:1-10] Seong-Soo Roh, Moon-Ki Park and Yong-ung Kim (2010). "Abietic Acid from Resina Pini of Pinus Species as a Testosterone 5α-Reductase Inhibitor". J. Health Sci. 56 (4): 451–455. doi:10.1248/jhs.56.451.

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