Abietic acid
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| Names | |
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| IUPAC name
Abieta-7,13-dien-18-oic acid
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.436 |
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| KEGG | |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C20H30O2 | |
| Molar mass | 302.458g·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)[2] |
| Boiling point | 250 °C; 482 °F; 523 K |
| Insoluble[2] | |
| Solubilityin other solvents | Very soluble in acetone, petroleum ether, Et2O, and ethanol |
| Hazards | |
| Occupational safety and health(OHS/OSH): | |
Main hazards
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Irritant |
| GHSlabelling: | |
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| Warning | |
| H317 | |
| P261,P272,P280,P302+P352,P321,P333+P313,P363,P501 | |
| NFPA 704(fire diamond) | |
| Safety data sheet(SDS) | MSDS |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Abietic acid(also known asabietinic acidorsylvic acid) is a mildorganic acidfound in coniferous trees.
It is a commercially important component of paints, soaps, foods, and solderingflux,and is the primary component ofresin acid.
Characteristics
[edit]Abietic acid is found in pine trees, including:
- Pinus insularis(Khasi Pine)
- Pinus kesiyaRoyle
- Pinus strobus(Eastern White Pine)
- Pinus sylvestris(Scots Pine).[3]
Pure abietic acid is a colorless solid, but commercial samples are usually a glassy or partlycrystallineyellowish solid that melts at temperatures as low as 85 °C (185 °F).[4]
Abietic acid is soluble inalcohols,acetone,andethers.Itsesterorsaltis called anabietate.[5]
Abietic acid belongs to theabietanediterpenegroup of organic compounds derived from fourisopreneunits.
Preparation
[edit]Abietic acid is extracted from treerosin[6](viaisomerization) and is the most abundant of several closely relatedorganic acidsthat constitute most ofrosin,the solid portion of theoleoresinofconiferous trees.
Resin acidsare converted intoester gumby reaction with controlled amounts ofglycerolor otherpolyhydric alcohols.
Uses
[edit]Abietic acid has drying properties, and asester gumis used inpaints,varnishes,andlacquers.[4]
It is also used insoaps,for the analysis ofresins,and the preparation of metal resinates.
As rosin
[edit]Rosin,of which abietic acid is the principal component:
- Has been used for centuries as afluxforsoldering.(Abietic acid in the flux removes oxidation from the surfaces of metals, increasing their ability to bond with the liquified solder.)
- Is rubbed on the hair of a violinbowto increase friction.
- Has been used for centuries forcaulkingships.[4]
- Is approved by the USFDAas a miscellaneous food additive.[7]
Safety
[edit]- As the chief component ofrosin,abietic acid is approved by the USFDAas a miscellaneous food additive.[7]
- Abietic acid is considered a "nonhazardous natural substance" intall oil( "liquid rosin" ).[5]
- In the U.S., abietic acid is listed in the inventory of theToxic Substances Control Act.
- Abietic acid is the primaryirritantinpinewood andresin.As acontact allergen[8]it is the cause ofabietic acid dermatitis.(However, compounds resulting from its oxidation by air elicit stronger responses.)[9]
- 50% ethanol extracts fromResina piniof Pinus sp. (Pinaceae) showed inhibitory activity againsttestosterone 5α-reductaseprepared from rat prostate. The fraction responsible for this activity was purified, and the active constituent was isolated and identified as abietic acid, which exhibited potentinhibitory activityagainst testosterone 5α-reductasein vitro.[10]
References
[edit]- ^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
- ^abMerck Index,12th Edition,3. Abietic Acid
- ^"Abietic Acid".Dr. Duke's Phytochemical and Ethnobotanical Databases.Archived fromthe originalon 2015-09-23.Retrieved13 January2012.
- ^abcHoiberg, Dale H., ed. (2010)."abietic acid".Encyclopædia Britannica.Vol. I: A-ak Bayes (15th ed.). Chicago, Illinois: Encyclopædia Britannica Inc. pp.32.ISBN978-1-59339-837-8.
- ^abLars-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;Collected Volumes,vol. 4, p. 1.
- ^abNutrition, 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.PMID7554886.S2CID36139468.
- ^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.PMID2096024.S2CID34726630.
- ^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.