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MedKoo Cat#: 145840 | Name: Guaiacin

Description:

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

Guaiacin is a lignan compound isolated from plants such as Machilus wangchiana and Cinnamomum philippinense. It has been studied for its potential pharmacological activities, including the inhibition of cyclooxygenase enzymes (COX-1 and COX-2), which play key roles in inflammation. By inhibiting these enzymes, guaiacin may help reduce inflammation, offering therapeutic benefits in conditions like arthritis. Additionally, guaiacin has been identified as a phosphatase activator, suggesting it may influence cellular signaling pathways.

Chemical Structure

Guaiacin
Guaiacin
CAS#36531-08-5

Theoretical Analysis

MedKoo Cat#: 145840

Name: Guaiacin

CAS#: 36531-08-5

Chemical Formula: C20H24O4

Exact Mass: 328.1700

Molecular Weight: 328.41

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Guaiacin;
IUPAC/Chemical Name
(6R,7S,8S)-8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
InChi Key
TZAAYUCUPIYQBR-JGRMJRGVSA-N
InChi Code
1S/C20H24O4/c1-11-7-14-9-19(24-4)17(22)10-15(14)20(12(11)2)13-5-6-16(21)18(8-13)23-3/h5-6,8-12,20-22H,7H2,1-4H3/t11-,12+,20+/m1/s1
SMILES Code
COC1=CC2=C(C=C1O)[C@@H]([C@@H](C)[C@H](C)C2)C3=CC(OC)=C(O)C=C3
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 328.41 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.

Recalculate based on batch purity %
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: Ahmad VU, Perveen S, Bano S. Guaiacin A and B from the Leaves of Guaiacum officinale. Planta Med. 1989 Jun;55(3):307-8. doi: 10.1055/s-2006-962014. PMID: 17262425. 2: Song Q, Wang J. Effects of the lignan compound (+)-Guaiacin on hair cell survival by activating Wnt/β-Catenin signaling in mouse cochlea. Tissue Cell. 2020 Oct;66:101393. doi: 10.1016/j.tice.2020.101393. Epub 2020 Jun 2. PMID: 32933716. 3: Lin SY, Ko HH, Lee SJ, Chang HS, Lin CH, Chen IS. Biological evaluation of secondary metabolites from the root of Machilus obovatifolia. Chem Biodivers. 2015 Jul;12(7):1057-67. doi: 10.1002/cbdv.201400196. PMID: 26172326. 4: Lee MK, Yang H, Ma CJ, Kim YC. Stimulatory activity of lignans from Machilus thunbergii on osteoblast differentiation. Biol Pharm Bull. 2007 Apr;30(4):814-7. doi: 10.1248/bpb.30.814. PMID: 17409528. 5: Ma CJ, Sung SH, Kim YC. Neuroprotective lignans from the bark of Machilus thunbergii. Planta Med. 2004 Jan;70(1):79-80. doi: 10.1055/s-2004-815463. PMID: 14765301. 6: Silva DH, Zhang Y, Santos LA, Bolzani VS, Nair MG. Lipoperoxidation and cyclooxygenases 1 and 2 inhibitory compounds from Iryanthera juruensis. J Agric Food Chem. 2007 Apr 4;55(7):2569-74. doi: 10.1021/jf063451x. Epub 2007 Mar 3. PMID: 17335225. 7: Cheng W, Zhu C, Xu W, Fan X, Yang Y, Li Y, Chen X, Wang W, Shi J. Chemical constituents of the bark of Machilus wangchiana and their biological activities. J Nat Prod. 2009 Dec;72(12):2145-52. doi: 10.1021/np900504a. PMID: 19916529. 8: Martinet A, Ndjoko K, Terreaux C, Marston A, Hostettmann K, Schutz Y. NMR and LC-MSn characterisation of two minor saponins from Ilex paraguariensis. Phytochem Anal. 2001 Jan-Feb;12(1):48-52. doi: 10.1002/1099-1565(200101/02)12:1<48::AID-PCA560>3.0.CO;2-#. PMID: 11704961. 9: Liu B, Liu M, Gan M, Zhao F, Wu X, Yu Y, Yue Z, Lin S, Wang S, Zhu C, Shi J. [Chemical constituents from roots of Machilus yaoshansis]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(9):1227-31. Chinese. PMID: 22803365. 10: Fo RB, de Carvalho MG, Gottlieb OR. XVIII: Eperudiendiol, Glycerides and Neolignans from Fruits of Osteophloeum platyspermum1. Planta Med. 1984 Feb;50(1):53-5. doi: 10.1055/s-2007-969620. PMID: 17340250. 11: 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. PMID: 24010288. 12: Amoss HL. ORGANIC MATTER IN THE EXPIRED BREATH WITH ESPECIAL REFERENCE TO ITS INHIBITING POWER ON OXIDIZING FERMENTS. J Exp Med. 1913 Feb 1;17(2):132-51. doi: 10.1084/jem.17.2.132. PMID: 19867631; PMCID: PMC2125023. 13: Yang XW, Huang X, Ahmat M. [New neolignan from seed of Myristica fragrans]. Zhongguo Zhong Yao Za Zhi. 2008 Feb;33(4):397-402. Chinese. PMID: 18533495. 14: Dang Z, Su S, Jin G, Nan X, Ma L, Li Z, Lu D, Ge R. Tsantan Sumtang attenuated chronic hypoxia-induced right ventricular structure remodeling and fibrosis by equilibrating local ACE-AngII-AT1R/ACE2-Ang1-7-Mas axis in rat. J Ethnopharmacol. 2020 Mar 25;250:112470. doi: 10.1016/j.jep.2019.112470. Epub 2019 Dec 17. PMID: 31862407.

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