Vulvic acid | Lauric acid | Dodecanoic Acid | GT-08 | CAS#143-07-7

MedKoo Cat#: 328034 | Name: Lauric acid

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lauric acid also known as Dodecanoic Acid and GT-08, is a proton pump inhibitor potentially for the treatment of helicobacter pylori infections. In vitro experiments have suggested that some fatty acids including lauric acid could be a useful component in a treatment for acne, but no clinical trials have yet been conducted to evaluate this potential benefit in humans. Lauric acid increases total serum cholesterol more than many other fatty acids. But most of the increase is attributable to an increase in high-density lipoprotein (HDL) (the "good" blood cholesterol). As a result, lauric acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid, either saturated or unsaturated.

Chemical Structure

Lauric acid

CAS#143-07-7

Theoretical Analysis

MedKoo Cat#: 328034

Name: Lauric acid

CAS#: 143-07-7

Chemical Formula: C12H24O2

Exact Mass: 200.1776

Molecular Weight: 200.32

Elemental Analysis: C, 71.95; H, 12.08; O, 15.97

Price and Availability

Size	Price	Availability	Quantity
25g	USD 250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Vulvic acid; Dodecanoic Acid; Lauric acid; GT-08; GT 08; GT08.

IUPAC/Chemical Name

Dodecanoic Acid

InChi Key

POULHZVOKOAJMA-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

SMILES Code

CCCCCCCCCCCC(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively.

In vitro activity:

Lauric acid induced apoptosis in Caco-2 (p < 0.05) and IEC-6 cells (p < 0.05) compared to butyrate. In Caco-2 cells, lauric acid reduced GSH availability and generated ROS compared to butyrate (p < 0.05). Lauric acid reduced Caco-2 and IEC-6 cells in G0/G1and arrested cells in the S and G2/M phases. Lauric acid induced apoptosis in IEC-6 cells compared to butyrate (p < 0.05). Reference: Chemotherapy. 2013;59(3):214-24. https://pubmed.ncbi.nlm.nih.gov/24356281/

In vivo activity:

Notably, both intradermal injection and epicutaneous application of lauric acid effectively decreased the number of P. acnes colonized with mouse ears, thereby relieving P. acnes-induced ear swelling and granulomatous inflammation. The obtained data highlight the potential of using lauric acid as an alternative treatment for antibiotic therapy of acne vulgaris. Reference: J Invest Dermatol. 2009 Oct;129(10):2480-8. https://pubmed.ncbi.nlm.nih.gov/19387482/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	149.76
	DMSO	103.3	515.84
	Ethanol	35.0	174.72
	Water	20.0	99.84

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 200.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wang J, Yang C, Hu X, Yao X, Han L, Wu X, Li R, Wen T, Ming L. Lauric Acid Induces Apoptosis of Rice Sheath Blight Disease Caused by Rhizoctonia solani by Affecting Fungal Fatty Acid Metabolism and Destroying the Dynamic Equilibrium of Reactive Oxygen Species. J Fungi (Basel). 2022 Feb 1;8(2):153. doi: 10.3390/jof8020153. PMID: 35205907; PMCID: PMC8875428. 2. Fauser JK, Matthews GM, Cummins AG, Howarth GS. Induction of apoptosis by the medium-chain length fatty acid lauric acid in colon cancer cells due to induction of oxidative stress. Chemotherapy. 2013;59(3):214-24. doi: 10.1159/000356067. Epub 2013 Dec 13. PMID: 24356281. 3. Kamoshita K, Tsugane H, Ishii KA, Takayama H, Yao X, Abuduwaili H, Tanida R, Taniguchi Y, Oo HK, Gafiyatullina G, Kaneko S, Matsugo S, Takamura T. Lauric acid impairs insulin-induced Akt phosphorylation by upregulating SELENOP expression via HNF4α induction. Am J Physiol Endocrinol Metab. 2022 May 2. doi: 10.1152/ajpendo.00163.2021. Epub ahead of print. PMID: 35499234. 4. Nakatsuji T, Kao MC, Fang JY, Zouboulis CC, Zhang L, Gallo RL, Huang CM. Antimicrobial property of lauric acid against Propionibacterium acnes: its therapeutic potential for inflammatory acne vulgaris. J Invest Dermatol. 2009 Oct;129(10):2480-8. doi: 10.1038/jid.2009.93. Epub 2009 Apr 23. PMID: 19387482; PMCID: PMC2772209.

In vitro protocol:

In vivo protocol:

1. Kamoshita K, Tsugane H, Ishii KA, Takayama H, Yao X, Abuduwaili H, Tanida R, Taniguchi Y, Oo HK, Gafiyatullina G, Kaneko S, Matsugo S, Takamura T. Lauric acid impairs insulin-induced Akt phosphorylation by upregulating SELENOP expression via HNF4α induction. Am J Physiol Endocrinol Metab. 2022 May 2. doi: 10.1152/ajpendo.00163.2021. Epub ahead of print. PMID: 35499234. 2. Nakatsuji T, Kao MC, Fang JY, Zouboulis CC, Zhang L, Gallo RL, Huang CM. Antimicrobial property of lauric acid against Propionibacterium acnes: its therapeutic potential for inflammatory acne vulgaris. J Invest Dermatol. 2009 Oct;129(10):2480-8. doi: 10.1038/jid.2009.93. Epub 2009 Apr 23. PMID: 19387482; PMCID: PMC2772209.

1: Lekshmi Sheela D, Nazeem PA, Narayanankutty A, Manalil JJ, Raghavamenon AC. In Silico and Wet Lab Studies Reveal the Cholesterol Lowering Efficacy of Lauric Acid, a Medium Chain Fat of Coconut Oil. Plant Foods Hum Nutr. 2016 Sep 27. PubMed PMID: 27679437. 2: McCarty MF, DiNicolantonio JJ. Lauric acid-rich medium-chain triglycerides can substitute for other oils in cooking applications and may have limited pathogenicity. Open Heart. 2016 Jul 27;3(2):e000467. doi: 10.1136/openhrt-2016-000467. Review. PubMed PMID: 27547436; PubMed Central PMCID: PMC4975867. 3: Uehara S, Uno Y, Ishii S, Inoue T, Sasaki E, Yamazaki H. Marmoset cytochrome P450 4A11, a novel arachidonic acid and lauric acid ω-hydroxylase expressed in liver and kidney tissues. Xenobiotica. 2016 Jul 20:1-9. PubMed PMID: 27435360. 4: Nonaka Y, Takagi T, Inai M, Nishimura S, Urashima S, Honda K, Aoyama T, Terada S. Lauric Acid Stimulates Ketone Body Production in the KT-5 Astrocyte Cell Line. J Oleo Sci. 2016 Aug 1;65(8):693-9. doi: 10.5650/jos.ess16069. PubMed PMID: 27430387. 5: Muniyan R, Gurunathan J. Lauric acid and myristic acid from Allium sativum inhibit the growth of Mycobacterium tuberculosis H37Ra: in silico analysis reveals possible binding to protein kinase B. Pharm Biol. 2016 Jun 16:1-8. PubMed PMID: 27307092. 6: Weng WH, Leung WH, Pang YJ, Hsu HH. Lauric acid can improve the sensitization of Cetuximab in KRAS/BRAF mutated colorectal cancer cells by retrievable microRNA-378 expression. Oncol Rep. 2016 Jan;35(1):107-16. doi: 10.3892/or.2015.4336. PubMed PMID: 26496897. 7: Silva EL, Carneiro G, De Araújo LA, Trindade Mde J, Yoshida MI, Oréfice RL, Farias Lde M, De Carvalho MA, Dos Santos SG, Goulart GA, Alves RJ, Ferreira LA. Solid Lipid Nanoparticles Loaded with Retinoic Acid and Lauric Acid as an Alternative for Topical Treatment of Acne Vulgaris. J Nanosci Nanotechnol. 2015 Jan;15(1):792-9. PubMed PMID: 26328443. 8: Zaloga J, Stapf M, Nowak J, Pöttler M, Friedrich RP, Tietze R, Lyer S, Lee G, Odenbach S, Hilger I, Alexiou C. Tangential Flow Ultrafiltration Allows Purification and Concentration of Lauric Acid-/Albumin-Coated Particles for Improved Magnetic Treatment. Int J Mol Sci. 2015 Aug 14;16(8):19291-307. doi: 10.3390/ijms160819291. PubMed PMID: 26287178; PubMed Central PMCID: PMC4581297. 9: Work VH, Melnicki MR, Hill EA, Davies FK, Kucek LA, Beliaev AS, Posewitz MC. Lauric Acid Production in a Glycogen-Less Strain of Synechococcus sp. PCC 7002. Front Bioeng Biotechnol. 2015 Apr 24;3:48. doi: 10.3389/fbioe.2015.00048. PubMed PMID: 25964950; PubMed Central PMCID: PMC4408914. 10: Yamashita S, Igarashi M, Hayashi C, Shitara T, Nomoto A, Mizote T, Shibasaki M. Identification of self-growth-inhibiting compounds lauric acid and 7-(Z)-tetradecenoic acid from Helicobacter pylori. Microbiology. 2015 Jun;161(6):1231-9. doi: 10.1099/mic.0.000077. PubMed PMID: 25767109. 11: Zaloga J, Janko C, Nowak J, Matuszak J, Knaup S, Eberbeck D, Tietze R, Unterweger H, Friedrich RP, Duerr S, Heimke-Brinck R, Baum E, Cicha I, Dörje F, Odenbach S, Lyer S, Lee G, Alexiou C. Development of a lauric acid/albumin hybrid iron oxide nanoparticle system with improved biocompatibility. Int J Nanomedicine. 2014 Oct 20;9:4847-66. doi: 10.2147/IJN.S68539. PubMed PMID: 25364244; PubMed Central PMCID: PMC4211907. 12: Rajesh PP, Noori MT, Ghangrekar MM. Controlling methanogenesis and improving power production of microbial fuel cell by lauric acid dosing. Water Sci Technol. 2014;70(8):1363-9. doi: 10.2166/wst.2014.386. PubMed PMID: 25353941. 13: Kim D, Cha GS, Nagy LD, Yun CH, Guengerich FP. Kinetic analysis of lauric acid hydroxylation by human cytochrome P450 4A11. Biochemistry. 2014 Oct 7;53(39):6161-72. doi: 10.1021/bi500710e. PubMed PMID: 25203493; PubMed Central PMCID: PMC4188250. 14: Jamuna-Thevi K, Saarani NN, Abdul Kadir MR, Hermawan H. Triple-layered PLGA/nanoapatite/lauric acid graded composite membrane for periodontal guided bone regeneration. Mater Sci Eng C Mater Biol Appl. 2014 Oct;43:253-63. doi: 10.1016/j.msec.2014.07.028. PubMed PMID: 25175212. 15: Chang F, He X, Fu X, Huang Q, Jane JL. Effects of heat treatment and moisture contents on interactions between lauric acid and starch granules. J Agric Food Chem. 2014 Aug 6;62(31):7862-8. doi: 10.1021/jf501606w. PubMed PMID: 25056554. 16: Faciola AP, Broderick GA. Effects of feeding lauric acid or coconut oil on ruminal protozoa numbers, fermentation pattern, digestion, omasal nutrient flow, and milk production in dairy cows. J Dairy Sci. 2014;97(8):5088-100. doi: 10.3168/jds.2013-7653. PubMed PMID: 24931520. 17: Zhao L, Hu Y, Xu D, Cai K. Surface functionalization of titanium substrates with chitosan-lauric acid conjugate to enhance osteoblasts functions and inhibit bacteria adhesion. Colloids Surf B Biointerfaces. 2014 Jul 1;119:115-25. doi: 10.1016/j.colsurfb.2014.05.002. PubMed PMID: 24880988. 18: Shankar S, Agarwal M, Chaurasia SP. Study of reaction parameters and kinetics of esterification of lauric acid with butanol by immobilized Candida antarctica lipase. Indian J Biochem Biophys. 2013 Dec;50(6):570-6. PubMed PMID: 24772983. 19: Pan H, Jiang B, Chen J, Jin Z. Blend-modification of soy protein/lauric acid edible films using polysaccharides. Food Chem. 2014 May 15;151:1-6. doi: 10.1016/j.foodchem.2013.11.075. PubMed PMID: 24423494. 20: Fauser JK, Matthews GM, Cummins AG, Howarth GS. Induction of apoptosis by the medium-chain length fatty acid lauric acid in colon cancer cells due to induction of oxidative stress. Chemotherapy. 2013;59(3):214-24. doi: 10.1159/000356067. PubMed PMID: 24356281.