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Chemistry (including Biochemistry)/Tea and coffee staining



I am trying to do a project on which household chemical is the best for removing coffee/ tea stains on shirts. They are referred as "oxidisable stains", can you explain more on the chemical reactions of that/ or the possible formulas?

Information online explains little on the chemistry of staining: presence of polyphenols/ theaflavins and thearubigins. I want to know if both coffee and tea have these, and whether there are other major chemicals causing the staining.

Moreover, the household chemicals I plan to use are: baking soda, hydrogen peroxide, water and vinegar. Any idea would the above be suitable choices? I am very weak in organic chemistry, would you mind telling me the reaction groups?

I would appreciate some readings if you find it more suitable.


Hello Hester!

I'll try to point you in the right directions: the whole answer would be pretty involved, and I think you'll remember more if you do some of the work on your own. If you get stuck, please feel free to come back and ask. :)

Coffee and tea are challenging to remove because of a class of compounds called tannins, as well as the polyphenol/flavonoid compounds you mentioned.

In organic chemistry, molecules are classified according to whether or not the atoms carry a charge. If there are lots of OH's and NH3's on a molecule, those atoms are charged. If the molecule has charge signs on it (positive or negative) it's a pretty good indicator that the molecules are charged (commonly known as 'polar'.) Chemists care about this because charged molecules will dissolve well in water. (Water is a very polar molecule - it is nothing but HOH groups! :) )

Some links:

Now if you look at the Wikipedia pages for a common fabric dye, Amaranth (, you see not only lots of SO4 groups (very polar) but lots of ring structures, too. Ring structures (if there's no letter, assume it's a C full up with hydrogens) and other plain C-H bonds are very non-polar: they do NOT like water. If you remove the SO4 groups from amaranth, it will permanently bind to natural fibers using those rings and color the fabric red.

Now look at the Wikipedia pages for these things, all of which are in coffee and tea to some amount:

All of these compounds can dissolve in water (but water can only 'carry' small amounts of them; it still doesn't like those rings.) The ring structures can bind/dye/stain fabric. This is very irksome when you dump tea on a white shirt.

What the 'oxidation' refers to is that given the presence of strong oxidizers, some molecules (like tannins) will find one another and form many many more chemical bonds. This makes it harder to remove the stain.

Vinegar is an acid, and contributes H+'s to solution. It is also a Lewis Acid, which means it likes to steal electron pairs. (
Baking soda is a base, and contributes OH-s to solution.  It is also a Lewis Base, which means it likes to donate electron pairs.

Electron pairs can form chemical bonds with other molecules, especially O and N atoms. Your experimental data will tell you if the acid or the base is better at getting the tannin rings off of the fibers.

Hydrogen Peroxide and Peroxides in general have extra electrons that can go and be donated to something. This tends to break established chemical bonds and rearrange them, sometimes breaking apart complex molecules. Your experimental data should tell you how peroxides do with stains. (

One last note. It might be worthwhile to seek out sodium borate (Borax). This is a laundry supplement and water softener that is known to soak out tannin-based stains. I believe it does this by the weak charges on the sodium borate ion interacting with the ring structures on the tannins, getting them to 'peel off' the fibers. It is an old-fashioned household chemical that might be a worthy addition to your testing strategy.

Good luck with your project!  

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Trista Robichaud, PhD


No homework questions, especially ones copied and pasted from textbooks. I will answer questions about principles or give hints, but I do not do other's homework. I'm comfortable answering basic biochemistry, chemistry, and biology questions up to and including an undergraduate level of understanding. This includes molecular biology, protein purification, and genetics. My training/inclination is primarily in structural biology, or how the shapes of things affect their function. Other interests include protein design, protein engineering, enzyme kinetics, and metabolic diseases such as cancer, atherosclerosis, and diabetes. My chemistry weaknesses are that I do not know organic or inorganic synthesis well, nor am I familiar with advanced inorganic reactions. I will attempt quantum mechanics and thermodynamics questions, but primarily as they relate to biological systems. Furthermore, I cannot tell you if a skin photograph is cancerous, or otherwise diagnose any disease. I can tell you how we currently understand the basic science behind a disease state, but I cannot recommend treatment in any way. Please direct such questions to your medical professional.


I hold a PhD in Biomedical Science from the University of Massachusetts Medical School in Worcester. I specialize in Biochemistry, with a focus on protein chemistry. My thesis work involved the structure and functions of the human glucose transporter 1. (hGLUT1) Currently I am a postdoc working in peptide (mini-protein) design and enzymology at the University of Texas Health Science Center in San Antonio, Texas. I am in Bjorn Steffensen's lab (PhD, DDS), studying gelatinase A and oral carcinoma.

2001 American Association for the Advancement of Science
2007 American Chemical Society
2007 Protein Society
2011 UTHSCSA Women’s Faculty Association

Levine KB, Robichaud TK, Hamill S, Sultzman LA, Carruthers A. Properties of the human erythrocyte glucose transport protein are determined by cellular context. Biochemistry 44(15):5606-16, 2005. (PMID 15823019)
Robichaud TK, Appleyard AN, Herbert RB, Henderson PJ, Carruthers A “Determinants of ligand binding affinity and cooperativity at the GLUT1 endofacial site” Biochemistry 50(15):3137-48, 2011. (PMID 21384913)
Xu X, Mikhailova M, Chen Z, Pal S, Robichaud TK, Lafer EM, Baber S, Steffensen B. “Peptide from the C-terminal domain of tissue inhibitor of matrix metalloproteinases-2 (TIMP-2) inhibits membrane activation of matrix metalloproteinase-2 (MMP-2)” Matrix Biol. 2011 Sep;30(7-8):404-12. (PMID: 21839835)
Robichaud TK, Steffensen B, Fields GB. Exosite interactions impact matrix metalloproteinase collagen specificities. J Biol Chem. 2011 Oct 28;286(43):37535-42 (PMID: 21896477)

Poster Abstracts:
Robichaud TK, Carruthers. A "Mutagenesis of the Human type 1 glucose transporter exit site: A functional study." ACS 234th Meeting, Boston MA. Division of Biological Chemistry, 2007
Robichaud TK, Bhowmick M, Tokmina-Roszyk D, Fields GB “Synthesis and Analysis of MT1-MMP Peptide Inhibitors” Biological Chemistry Division of the Protein Society Meeting, San Diego CA 2010
Robichaud TK; Tokmina-Roszyk D; Steffensen B and Fields GB “Catalytic Domain Exosites Contribute to Determining Matrix Metalloproteinase Triple Helical Collagen Specificities” Dental Science Symposium. UTHSCSA 2011
Robichaud TK; Tokmina-Roszyk D; Steffensen B and Fields GB “Exosite Interactions Determine Matrix Metalloproteinase Specificities” Gordon Research Conference on Matrix Metalloproteinase Biology, Bristol RI 2011

Oakland University, Auburn Hills MI BS, Biochemistry 1998
University of Massachusetts Medical School, Worcester MA PhD, Biochemistry & Molecular Pharmacology 2001-2008
University of Texas Health Science Center, San Antonio TX Postdoc, Biochemistry 2009-Present

Awards and Honors
1998 Honors College Graduate, Oakland University
2009 Institutional National Research Service Award, Pathobiology of Occlusive Vascular Disease T32 HL07446
2011 1st Place, Best Postdoctoral Poster, Dental Science Symposium, UTHSCSA, April 2011

Past/Present Clients
Invited Seminars:
Robichaud TK, Fields GB. “Synthesis and Analysis of MTI-MMP Triple Helical Peptide Inhibitors” Pathology Research Conference, University of Texas Health Science Center San Antonio Pathology Department (June 18th, 2010)
Robichaud TK & Hill, B “How To Give A Great Scientific Talk” Invited Lecture, Pathobiology of Occlusive Vascular Disease Seminars, UTHSCSA (Nov 11th 2010), Cardiology Seminar Series, Texas Research Park (Feb 21st, 2011)
Robichaud TK; Tokmina-Roszyk D; Steffensen B and Fields GB “Exosite Interactions Determine Matrix Metalloproteinase Specificities” Gordon-Keenan Research Seminar “Everything You Wanted to Know About Matrix Metalloproteinases But Were Afraid to Ask” Bristol, RI (Aug 6th, 2011)

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