meso-Dihydroguaiaretic acid | CAS#36469-60-0

MedKoo Cat#: 526594 | Name: meso-Dihydroguaiaretic acid

Description:

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

meso-Dihydroguaiaretic acid is an LXR-α antagonist, inhibiting hepatic lipid accumulation by activating AMP-activated protein kinase in human HepG2 cells.

Chemical Structure

meso-Dihydroguaiaretic acid

CAS#36469-60-0

Theoretical Analysis

MedKoo Cat#: 526594

Name: meso-Dihydroguaiaretic acid

CAS#: 36469-60-0

Chemical Formula: C20H26O4

Exact Mass: 330.1831

Molecular Weight: 330.42

Elemental Analysis: C, 72.70; H, 7.93; O, 19.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

meso-Dihydroguaiaretic acid

IUPAC/Chemical Name

4-[(2r,3s)-4-(4-Hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol

InChi Key

ADFOLUXMYYCTRR-OKILXGFUSA-N

InChi Code

InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+

SMILES Code

OC1=CC=C(C[C@@H](C)[C@@H](C)CC2=CC=C(O)C(OC)=C2)C=C1OC

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 330.42 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

1: Lee A, Choi KM, Jung WB, Jeong H, Kim GY, Lee JH, Lee MK, Hong JT, Roh YS, Sung SH, Yoo HS. Enhancement of Glucose Uptake by Meso-Dihydroguaiaretic Acid through GLUT4 Up-Regulation in 3T3-L1 Adipocytes. Molecules. 2017 Aug 28;22(9). pii: E1423. doi: 10.3390/molecules22091423. PubMed PMID: 28846649. 2: Reyes-Melo K, García A, Romo-Mancillas A, Garza-González E, Rivas-Galindo VM, Miranda LD, Vargas-Villarreal J, Favela-Hernández JMJ, Camacho-Corona MDR. meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity. Bioorg Med Chem. 2017 Oct 15;25(20):5247-5259. doi: 10.1016/j.bmc.2017.07.047. Epub 2017 Jul 29. PubMed PMID: 28844400. 3: Nishiwaki H, Nakazaki S, Akiyama K, Yamauchi S. Structure-Antifungal Activity Relationship of Fluorinated Dihydroguaiaretic Acid Derivatives and Preventive Activity against Alternaria alternata Japanese Pear Pathotype. J Agric Food Chem. 2017 Aug 9;65(31):6701-6707. doi: 10.1021/acs.jafc.7b01896. Epub 2017 Jul 26. PubMed PMID: 28681599. 4: Vuorinen A, Engeli RT, Leugger S, Bachmann F, Akram M, Atanasov AG, Waltenberger B, Temml V, Stuppner H, Krenn L, Ateba SB, Njamen D, Davis RA, Odermatt A, Schuster D. Potential Antiosteoporotic Natural Product Lead Compounds That Inhibit 17β-Hydroxysteroid Dehydrogenase Type 2. J Nat Prod. 2017 Apr 28;80(4):965-974. doi: 10.1021/acs.jnatprod.6b00950. Epub 2017 Mar 20. PubMed PMID: 28319389; PubMed Central PMCID: PMC5411959. 5: Jeong M, Kim HM, Kim HJ, Choi JH, Jang DS. Kudsuphilactone B, a nortriterpenoid isolated from Schisandra chinensis fruit, induces caspase-dependent apoptosis in human ovarian cancer A2780 cells. Arch Pharm Res. 2017 Apr;40(4):500-508. doi: 10.1007/s12272-017-0902-5. Epub 2017 Feb 22. PubMed PMID: 28229391. 6: Nakano Y, Nasu M, Kano M, Kameoka H, Okuyama T, Nishizawa M, Ikeya Y. Lignans from guaiac resin decrease nitric oxide production in interleukin 1β-treated hepatocytes. J Nat Med. 2017 Jan;71(1):190-197. doi: 10.1007/s11418-016-1048-3. Epub 2016 Oct 5. PubMed PMID: 27709321. 7: Yamauchi S, Tanimura R, Nishiwaki H, Nishi K, Sugahara T, Maruyama M, Ano Y, Akiyama K, Kishida T. Enantioselective syntheses of both enantiomers of 9'-dehydroxyimperanene and 7,8-dihydro-9'-dehydroxyimperanene and the comparison of biological activity between 9-norlignans and dihydroguaiaretic acids. Bioorg Med Chem Lett. 2016 Jul 1;26(13):3019-3023. doi: 10.1016/j.bmcl.2016.05.020. Epub 2016 May 7. PubMed PMID: 27210431. 8: Song JW, Seo CS, Cho ES, Kim TI, Won YS, Kwon HJ, Son JK, Son HY. meso-Dihydroguaiaretic acid attenuates airway inflammation and mucus hypersecretion in an ovalbumin-induced murine model of asthma. Int Immunopharmacol. 2016 Feb;31:239-47. doi: 10.1016/j.intimp.2015.12.033. Epub 2016 Jan 11. PubMed PMID: 26773771. 9: Choi MS, Jeong HJ, Kang TH, Shin HM, Oh ST, Choi Y, Jeon S. Meso-dihydroguaiaretic acid induces apoptosis and inhibits cell migration via p38 activation and EGFR/Src/intergrin β3 downregulation in breast cancer cells. Life Sci. 2015 Nov 15;141:81-9. doi: 10.1016/j.lfs.2015.09.003. Epub 2015 Sep 14. PubMed PMID: 26382595. 10: Zheng LS, Du SS, Cai Q. [Study on chemical constituents from Schisandra chinensis stem]. Zhong Yao Cai. 2014 Oct;37(10):1803-6. Chinese. PubMed PMID: 25895389. 11: Jeong HJ, Koo BS, Kang TH, Shin HM, Jung S, Jeon S. Inhibitory effects of Saururus chinensis and its components on stomach cancer cells. Phytomedicine. 2015 Feb 15;22(2):256-61. doi: 10.1016/j.phymed.2014.12.003. Epub 2014 Dec 19. PubMed PMID: 25765830. 12: Nishiwaki H, Tabara Y, Kishida T, Nishi K, Shuto Y, Sugahara T, Yamauchi S. Acute larvicidal activity against mosquitoes and oxygen consumption inhibitory activity of dihydroguaiaretic acid derivatives. J Agric Food Chem. 2015 Mar 11;63(9):2442-8. doi: 10.1021/jf504816a. Epub 2015 Feb 24. PubMed PMID: 25669766. 13: Jeon JS, Oh SJ, Lee JY, Ryu CS, Kim YM, Lee BH, Kim SK. Metabolic characterization of meso-dihydroguaiaretic acid in liver microsomes and in mice. Food Chem Toxicol. 2015 Feb;76:94-102. doi: 10.1016/j.fct.2014.12.007. Epub 2014 Dec 19. PubMed PMID: 25533794. 14: Zhang J, Wang ZM, Liu KC, He QX, Qi YD, Zhang BG, Liu HT, Xiao PG. [Chemical constituents of Kadsura oblongifolia and evaluation of their toxicity]. Yao Xue Xue Bao. 2014 Sep;49(9):1296-303. Chinese. PubMed PMID: 25518329. 15: Clemente-Soto AF, Balderas-Rentería I, Rivera G, Segura-Cabrera A, Garza-González E, del Rayo Camacho-Corona M. Potential mechanism of action of meso-dihydroguaiaretic acid on Mycobacterium tuberculosis H37Rv. Molecules. 2014 Dec 2;19(12):20170-82. doi: 10.3390/molecules191220170. PubMed PMID: 25474289. 16: Song MC, Kim EC, Kim WJ, Kim TJ. Meso-dihydroguaiaretic acid inhibits rat aortic vascular smooth muscle cell proliferation by suppressing phosphorylation of platelet-derived growth factor receptor beta. Eur J Pharmacol. 2014 Dec 5;744:36-41. doi: 10.1016/j.ejphar.2014.09.029. Epub 2014 Sep 23. PubMed PMID: 25261039. 17: Sim WC, Park S, Lee KY, Je YT, Yin HQ, Choi YJ, Sung SH, Park SJ, Park HJ, Shin KJ, Lee BH. LXR-α antagonist meso-dihydroguaiaretic acid attenuates high-fat diet-induced nonalcoholic fatty liver. Biochem Pharmacol. 2014 Aug 15;90(4):414-24. doi: 10.1016/j.bcp.2014.06.013. Epub 2014 Jun 21. PubMed PMID: 24955981. 18: Wukirsari T, Nishiwaki H, Nishi K, Sugahara T, Akiyama K, Kishida T, Yamauchi S. Cytotoxic activity of dietary lignan and its derivatives: structure-cytotoxic activity relationship of dihydroguaiaretic acid. J Agric Food Chem. 2014 Jun 11;62(23):5305-15. doi: 10.1021/jf5010572. Epub 2014 Jun 3. PubMed PMID: 24841776. 19: Minh PT, Lam do T, Tien NQ, Tuan NN, Nhung VP, Van Hai N, Van Kiem P, Nhiem NX, Van Minh C, Ju PS, Hyun KS. New schiartane-type triterpene from Kadsura heteroclita and their cytotoxic activities. Nat Prod Commun. 2014 Mar;9(3):373-4. PubMed PMID: 24689220. 20: Bu PB, Li YR, Jiang M, Wang XL, Wang F, Lin S, Zhu CG, Shi JG. [Lignans from Machilus robusta]. Zhongguo Zhong Yao Za Zhi. 2013 Jun;38(11):1740-6. Chinese. PubMed PMID: 24010288.