Abietic acid

Abietic acid (also known as abietinic acid or sylvic acid) is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin (via isomerization) and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees. Its ester or salt is called an abietate.[2]

Abietic acid
Names
IUPAC name
Abieta-7,13-dien-18-oic acid
Other names
(1R,4aR,4bR,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid; Abietinic acid; Sylvic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.436
EC Number
  • 208-173-3
KEGG
RTECS number
  • TP8580000
UNII
Properties
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) [1]
Insoluble[1]
Solubility in other solvents Very soluble in acetone, petroleum ether, Et2O, and ethanol
Hazards
Main hazards Irritant
Safety data sheet MSDS
GHS pictograms
GHS Signal word Warning
H317
P261, P272, P280, P302+352, P321, P333+313, P363, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Preparation

Abietic acid is extracted from tree rosin.[3] The pure material 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]

It belongs to the abietane diterpene group of organic compounds derived from four isoprene units. It is used in lacquers, varnishes, and soaps, and for the analysis of resins and the preparation of metal resinates. It is found in Pinus insularis (Khasi Pine), Pinus kesiya Royle, Pinus strobus (Eastern White Pine), and Pinus sylvestris (Scots Pine).[5]

Uses

Rosin has been used for centuries for caulking ships.[4] It is also rubbed on the bows of musical instruments to make them less slippery.[4] In modern times methods have been developed for improving the properties of the rosin acids, which are otherwise soft, tacky, and low-melting and subject to rapid deterioration by oxidation in air. Stability is greatly increased by heat treatment.

Resin acids are converted into ester gum by reaction with controlled amounts of glycerol or other polyhydric alcohols. Ester gum has drying properties and is used in paints, varnishes, and lacquers.[4]

Rosin has been used to depackage integrated circuits from their epoxy coatings.[6]

In vitro effects

The 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 testosterone 5α-reductase inhibitory activity in vitro.[7]

Safety

Abietic acid is considered a "nonhazardous natural substance" in tall oil.[2] In the U.S., it is listed in the Toxic Substances Control Act inventory. Abietic acid is a contact allergen;[8] however, compounds resulting from its oxidation by air elicit stronger responses.[9] It is soluble in alcohols, acetone, and ethers.

References
  1. Merck Index, 12th Edition, 3. Abietic Acid
  2. Lars-Hugo Norlin "Tall Oil" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a26_057
  3. G. C. Harris and T. F. Sanderson (1963). "Abietic Acid". Organic Syntheses. 32: 1.; Collective Volume, 4, p. 1
  4. Hoiberg, Dale H., ed. (2010). "abietic acid". Encyclopædia Britannica. I: A-ak Bayes (15th ed.). Chicago, Illinois: Encyclopædia Britannica Inc. pp. 32. ISBN 978-1-59339-837-8.
  5. "Abietic Acid". Dr. Duke's Phytochemical and Ethnobotanical Databases. Archived from the original on 2015-09-23. Retrieved 13 January 2012.
  6. "Deencapsulation of ICs using heated rosin". Archived from the original on 2014-07-24. Retrieved 2014-04-16.
  7. 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.
  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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.