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] As the chief component of rosin, it is approved by FDA as a miscellaneous food additive.[3]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.436
EC Number
  • 208-173-3
KEGG
RTECS number
  • TP8580000
UNII
  • 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 checkY
    Key: RSWGJHLUYNHPMX-ONCXSQPRSA-N checkY
  • 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
  • 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
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]
Boiling point 250 °C; 482 °F; 523 K
Insoluble[1]
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:
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored 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).
checkY verify (what is checkY☒N ?)
Infobox references

Preparation

Abietic acid is extracted from tree rosin.[4] 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).[5]

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).[6]

Uses

Rosin has been used for centuries for caulking ships.[5] It is also rubbed on the bows of musical instruments to make them less slippery.[5] 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.[5]

Rosin has been used to depackage integrated circuits from their epoxy coatings.[7] It is also used as a core for tin solder wire in order to increase the flow of the melted tin when heat is applied.

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.[8]

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;[9] however, compounds resulting from its oxidation by air elicit stronger responses.[10] It is soluble in alcohols, acetone, and ethers.

As the chief component of rosin, abietic acid is approved by FDA as a miscellaneous food additive.[3] This approval requires a review in light of the 2010 research on abietic acid's potent testosterone 5α-reductase inhibitory activity in vitro.[8] Testosterone 5α-reductase biochemical substrates are several major hormones in humans, such as sex hormones, cortisol, and aldosterone. Fetal inhibition of cortisol is associated to autism-like developmental defects.[11] Low testosterone levels are associated with obesity.[12][13][14] Abietic acid, as part of rosin gum, may be in general consumption since big names such as Coca-Cola Company are rosin gum consumers, and it's unclear whether it's used in recipes (company secret) but they use only FDA approved substances.

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. Nutrition, Center for Food Safety and Applied (2022-08-25). "Food Additive Status List". FDA.
  4. G. C. Harris and T. F. Sanderson (1963). "Abietic Acid". Organic Syntheses. 32: 1.; Collective Volume, vol. 4, p. 1
  5. 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.
  6. "Abietic Acid". Dr. Duke's Phytochemical and Ethnobotanical Databases. Archived from the original on 2015-09-23. Retrieved 13 January 2012.
  7. "Deencapsulation of ICs using heated rosin". Archived from the original on 2014-07-24. Retrieved 2014-04-16.
  8. 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.
  9. 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.
  10. 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.
  11. Ram, Sheena; Howland, Mariann A.; Sandman, Curt A.; Davis, Elysia Poggi; Glynn, Laura M. (2019-03-01). "Prenatal Risk for ASD: Fetal Cortisol Exposure Predicts Child Autism-Spectrum Disorder Symptoms". Clinical Psychological Science. 7 (2): 349–361. doi:10.1177/2167702618811079. ISSN 2167-7026. PMC 7983844. PMID 33758678.
  12. Kelly, D. M.; Jones, T. H. (July 2015). "Testosterone and obesity". Obesity Reviews. 16 (7): 581–606. doi:10.1111/obr.12282. ISSN 1467-789X. PMID 25982085. S2CID 25605729.
  13. Fui, Mark Ng Tang; Dupuis, Philippe; Grossmann, Mathis (2014). "Lowered testosterone in male obesity: mechanisms, morbidity and management". Asian Journal of Andrology. 16 (2): 223–231. doi:10.4103/1008-682X.122365. ISSN 1745-7262. PMC 3955331. PMID 24407187.
  14. Caliber, Monica; Saad, Farid (October 2020). "Testosterone Therapy for Prevention and Treatment of Obesity in Men". Androgens: Clinical Research and Therapeutics. 1 (1): 40–61. doi:10.1089/andro.2020.0010. S2CID 225144622.
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