LeClaire Institute

Module 2 · Water-Soluble Vitamins

The second micronutrient lesson covers the nine water-soluble vitamins: the eight B vitamins and vitamin C. Unlike A, D, E and K, they dissolve in water, are stored only in small amounts (except B12) and are easily lost in cooking. The B vitamins all become coenzymes, small helpers that let enzymes release energy and build new cells. Each is shown as a ball-and-stick model with what it does, what happens with too little or too much, and where to find it in whole foods, including the difference between folate and folic acid. The figure is on the left and the lesson script on the right; the quiz is at the end.

Previous lesson: Module 2 · Fat-Soluble Vitamins

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Figure 1

The Water-Soluble Vitamin Family Tree

Eight B vitamins and vitamin C.

What they share
Covered in N and OTheir many oxygen and nitrogen atoms form hydrogen bonds with water, so they dissolve in it, unlike vitamins A, D, E and K.
Little storageApart from B12, the body keeps only small reserves and passes extra in urine, so a steady supply from food matters.
Easily lost in cookingThey leach into cooking water, and several (C, folate, thiamin) are damaged by heat; riboflavin is damaged by light (Figure 8).
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Figure 2

Coenzymes: What B Vitamins Do

Small helpers that let enzymes work.

What a coenzyme is
  1. Enzymes run your chemistryproteins that speed up reactions, such as releasing energy from glucose and fat
  2. Many need a helpera small non-protein partner that carries electrons, carbon or other groups
  3. B vitamins become those helperseach is changed slightly in the body, often by adding phosphate
  4. Reused, not burneda little goes a long way, so needs are in milligrams or micrograms
Each B vitamin and its coenzyme
VitaminBecomesCarries or does
B1 thiaminthiamin pyrophosphate (TPP)cuts carbon chains in carbohydrate breakdown
B2 riboflavinFAD and FMNcarries electrons (hydrogens)
B3 niacinNAD and NADPcarries electrons; used in hundreds of reactions
B5 pantothenic acidcoenzyme Acarries two-carbon acetyl groups
B6pyridoxal phosphate (PLP)moves amino groups between amino acids
B7 biotinbiotin bound to enzymesadds CO2 to molecules
B9 folatetetrahydrofolate (THF)carries one-carbon units for DNA building blocks
B12methylcobalamin, adenosylcobalaminrecycles folate; one step of fat and amino-acid breakdown
The B vitamins don’t give energy
A common mix-upB vitamins contain no usable calories. They are the tools that let your cells release the energy in carbohydrate, fat and protein, so a shortage makes you tired, but extra doesn’t make you more energetic.
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Figure 3

B1, B2 and B3

Thiamin, riboflavin and niacin: energy release.

B1: thiamin

Thiamin (vitamin B1), C12H17N4OS+

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  1. 1A pyrimidine ring (two N atoms) with an NH2.
  2. 2A thiazole ring with sulfur (yellow); the positive N is part of the business end. Thiamin is one of only two vitamins with sulfur (biotin is the other).
  3. 3The OH is where two phosphates are added to make the coenzyme TPP.

In your body: As TPP, needed to break down glucose for energy and for nerve function. RDA 1.2 mg (men), 1.1 mg (women).

Too little: Beriberi: nerve damage, muscle weakness, heart failure. In heavy drinkers, a brain disorder (Wernicke-Korsakoff syndrome).

Found in: Pork, trout, black beans, lentils, whole grains, sunflower seeds.

B2: riboflavin

Riboflavin (vitamin B2), C17H20N4O6

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  1. 1Three flat rings that can take up and release two hydrogens: this is how FAD carries electrons. They make riboflavin bright yellow.
  2. 2A ribitol chain, a sugar alcohol with four OH groups.

In your body: As FAD and FMN, carries electrons in energy production. RDA 1.3 mg (men), 1.1 mg (women). Extra turns urine bright yellow, which is harmless.

Too little: Cracks at the corners of the mouth, sore red tongue, sore throat.

Found in: Milk, yogurt, eggs, liver, almonds, mushrooms. Light destroys it, which is why milk is sold in opaque containers.

B3: niacin

Niacin (vitamin B3): two forms

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Nicotinic acidC6H5NO2

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NicotinamideC6H6N2O

  1. 1Nicotinic acid ends in COOH…
  2. 2…nicotinamide in CONH2. Both make NAD, the most widely used coenzyme in the body.

In your body: As NAD and NADP, used in hundreds of reactions. Your body can also make niacin from the amino acid tryptophan. RDA 16 mg (men), 14 mg (women).

Too little: Pellagra: rough, dark skin rash in sunlight, diarrhea, confusion.

Too much: Supplements of nicotinic acid above about 35 mg cause flushing; large doses can harm the liver. Food doesn’t cause this.

Found in: Tuna, chicken, turkey, salmon, peanuts, mushrooms, brown rice.

carbon hydrogen oxygen nitrogen sulfur · every molecule on this page is drawn at the same scale with every hydrogen shown · tap one to enlarge it

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Figure 4

B5 and B7

Pantothenic acid and biotin.

B5: pantothenic acid

Pantothenic acid (vitamin B5), C9H17NO5

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  1. 1An amide link, like a peptide bond, joins two small pieces.
  2. 2The acid end. In the body it is built into coenzyme A, which carries two-carbon pieces in and out of the energy cycle.

What it is: Its name means “from everywhere”: almost every food has some.

In your body: Part of coenzyme A, needed to make and break down fats and to release energy. Adequate intake 5 mg a day.

Too little: Very rare; seen only in severe starvation or experiments: numbness and burning feet, fatigue.

Found in: Liver, chicken, mushrooms, avocado, eggs, sunflower seeds, whole grains.

B7: biotin

Biotin (vitamin B7), C10H16N2O3S

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  1. 1The ring with two NH groups is where CO2 is attached and handed on.
  2. 2The sulfur ring.
  3. 3The acid tail links biotin firmly to its enzymes.

In your body: Helps enzymes add CO2 to molecules, in making fat, glucose and some amino acids. Adequate intake 30 µg a day.

Too little: Rare: thinning hair, red scaly rash. Avidin in raw egg white binds biotin, but only large amounts of raw whites over long periods cause a problem; cooking destroys avidin.

Too much: No harm known, but high-dose supplements can distort some blood tests, including thyroid and heart tests.

Found in: Egg yolks, liver, salmon, sunflower seeds, almonds, sweet potato.

carbon hydrogen oxygen nitrogen sulfur · every molecule on this page is drawn at the same scale with every hydrogen shown · tap one to enlarge it

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Figure 5

B6 and Folate

Amino acids, DNA, and folate versus folic acid.

B6

Pyridoxine (vitamin B6), C8H11NO3

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  1. 1A pyridine ring: a benzene-like ring with one nitrogen.
  2. 2In the body this CH2OH becomes an aldehyde and a phosphate is added, making pyridoxal phosphate (PLP), the working coenzyme.

In your body: As PLP, needed by over 100 enzymes, mostly in amino-acid metabolism; also for making neurotransmitters and hemoglobin. RDA 1.3 mg for adults up to 50, then 1.7 mg (men) and 1.5 mg (women).

Too little: Anemia, cracked lips, sore tongue, depression and confusion.

Too much: Long-term supplements above the upper limit (100 mg a day) can cause nerve damage in the hands and feet.

Found in: Chickpeas, tuna, salmon, chicken, potatoes, bananas.

B9: folate

Folic acid and food folate

Folic acid (the form added to foods), C19H19N7O6

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5-Methyltetrahydrofolate (the main form in food and blood), C20H25N7O6

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  1. 1Pterin: two rings rich in nitrogen.
  2. 2Para-aminobenzoic acid: a benzene ring linking the two ends.
  3. 3Glutamate, an amino acid. Food folates usually carry a chain of several glutamates, trimmed off in the gut.
  4. 4Four more hydrogens here (tetrahydro): this reduced ring is the active form that carries one-carbon units.
  5. 5A methyl group: the one-carbon unit, ready to hand on (to B12, Figure 6).

Folate vs folic acid: “folate” covers all the natural forms. Folic acid is the synthetic, fully oxidized form: very stable and better absorbed (about 1.7 times as well as food folate), so it is used in supplements and fortified flour. The body must add the four hydrogens before it can use it.

In your body: Carries one-carbon units to build DNA and to recycle the amino acid homocysteine; essential for cell division. RDA 400 µg DFE (dietary folate equivalents); 600 µg in pregnancy.

Too little: Megaloblastic anemia (large, immature red cells). Before and early in pregnancy, low folate raises the risk of neural tube defects such as spina bifida, which is why folic acid is recommended for anyone who could become pregnant.

Too much: No harm known from food folate. Folic acid above the upper limit (1,000 µg a day) can hide the anemia of B12 deficiency while its nerve damage continues.

Found in: Lentils, chickpeas, black-eyed peas, spinach, asparagus, Brussels sprouts, avocado, liver. Its name comes from Latin folium, leaf.

carbon hydrogen oxygen nitrogen · every molecule on this page is drawn at the same scale with every hydrogen shown · tap one to enlarge it

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Figure 6

Vitamin B12

The cobalt vitamin, and who runs short.

Vitamin B12 (cobalamin)

A big molecule built around cobalt

B12 is the largest and most complex vitamin: about 180 atoms (cyanocobalamin is C63H88CoN14O14P), too big to draw atom by atom at this page’s scale. At its heart is a cobalt atom (pink) held by four nitrogens (blue) of a ring of four linked five-membered rings, the corrin ring (gray), seen here at a slant. Below, a long tail loops round so that a nitrogen at its end (blue, below) holds the cobalt from underneath. The group on top (orange) varies: methyl or adenosyl in the body’s two coenzymes, hydroxo in food, cyano in most supplements.

Cartoon, not to scale.

How B12 is absorbed
  1. In foodB12 is bound to protein
  2. Stomachacid and enzymes release it
  3. Intrinsic factora protein made by the stomach lining binds the B12
  4. End of the small intestinethe pair is taken up together
  5. Storedthe liver keeps a supply that can last several years
Who runs short
VegansOnly bacteria make B12, and it reaches us through animal foods. Plant foods don’t provide reliable amounts, so vegans need fortified foods or a supplement.
Older adultsMany have less stomach acid and absorb less B12 from food; the synthetic form in fortified foods and supplements is absorbed more easily.
People without intrinsic factorPernicious anemia, an autoimmune condition, or stomach surgery stops absorption; treatment is by injection or high doses, under a doctor’s care.

Vitamin B12 at a glance

In your body: Works with folate to make DNA and red blood cells; keeps the nerves’ insulating sheath healthy. RDA 2.4 µg a day.

Too little: Megaloblastic anemia and fatigue; numbness, tingling, balance problems and memory changes that can become permanent.

Too much: No harm known from food or supplements, so there is no upper limit.

Found in: Clams, liver, sardines, salmon, beef, eggs, milk, yogurt, cheese.

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Figure 7

Vitamin C

Ascorbic acid: collagen, iron and antioxidant.

Vitamin C

Vitamin C: ascorbic acid and its oxidized form

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Ascorbic acidC6H8O6

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Dehydroascorbic acidC6H6O6

  1. 1Two OH groups on a C=C: they give up two hydrogens (with their electrons) very easily. That is what makes vitamin C an antioxidant and a helper for enzymes.
  2. 2After giving them up, both carbons carry a C=O: dehydroascorbic acid. Your cells can take it up and turn it back into ascorbic acid.
  3. 3Four OH groups in all: very water-soluble.

What it is: Humans, along with a few other animals such as guinea pigs, can’t make vitamin C, because the gene for the last enzyme of the pathway no longer works.

In your body: RDA 90 mg (men), 75 mg (women); smokers need 35 mg more.

Too little: Scurvy, after about a month of very low intake: tiredness, bleeding and swollen gums, easy bruising, slow wound healing.

Too much: Above the upper limit (2,000 mg a day, from supplements), diarrhea and stomach upset; possibly kidney stones in some people.

Found in: Bell peppers, kiwi, oranges and other citrus, strawberries, broccoli, Brussels sprouts, tomatoes, potatoes.

What vitamin C does
CollagenEnzymes that make collagen, the protein of skin, gums, tendons and blood vessels, need vitamin C to stay active.
IronIt turns plant (non-heme) iron into a form that is absorbed more easily when eaten in the same meal.
AntioxidantIt mops up reactive molecules in water-based parts of the body and helps restore vitamin E.

carbon hydrogen oxygen · every molecule on this page is drawn at the same scale with every hydrogen shown · tap one to enlarge it

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Figure 8

Cooking and Labels

What destroys them, and the forms on labels.

Cooking and storage
VitaminDamaged byTo keep more
C, folate, thiaminheat; also leach into cooking watersteam or microwave briefly; use less water; eat some fruit and vegetables raw
Riboflavinlightstore milk and grains out of light
B12, niacin, biotinfairly stable—
Forms you will see
On the label or ingredient listVitamin
Thiamin mononitrate, thiamin hydrochlorideB1
RiboflavinB2 (also a yellow color, E101)
Niacin, niacinamide (nicotinamide)B3
Calcium pantothenateB5
Pyridoxine hydrochlorideB6
BiotinB7
Folic acid; L-methylfolateB9
Cyanocobalamin, methylcobalaminB12
Ascorbic acid, sodium ascorbate (E300, E301)C; also used as an antioxidant to stop browning
Enriched and fortified
Enriched flourIn the US, refined wheat flour is usually enriched: thiamin, riboflavin, niacin and iron are added back after milling removes them, and folic acid has been required in enriched grain products since 1998.
Folate on the labelFolate is listed in µg DFE; if folic acid is added, the label also shows the amount of folic acid in parentheses.
Daily ValuesThiamin 1.2 mg, riboflavin 1.3 mg, niacin 16 mg, B6 1.7 mg, folate 400 µg DFE, B12 2.4 µg, biotin 30 µg, pantothenic acid 5 mg, vitamin C 90 mg.
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Figure 9

Where water-soluble vitamins are used in the body

Tap a number on the cell to see what that part does; the list below it gives every other place in the body.

The B vitamins and vitamin C work in every cell; extra leaves in the urine, except B12, which the liver stores.

Inside a cell

A typical animal cell, not to scale. Real cells hold thousands of ribosomes and hundreds of mitochondria.

B vitamins are helpers for energy enzymes; vitamin C keeps other enzymes working.

  1. Thiamin (B1), riboflavin (B2), niacin (B3), pantothenic acid (B5) and biotin help the enzymes that burn fuel to make ATP; B12 helps one enzyme here that processes some fats and amino acids.
  2. B6 helps enzymes that move amino-acid groups; niacin (as NAD) also runs glycolysis.
  3. Folate carries the carbon pieces needed to build DNA, and with B12 it keeps up the supply of methyl tags that mark DNA.
  4. Vitamin C keeps the enzymes that finish collagen working, so its fibers are strong.
  5. Carrier proteins bring each vitamin in; vitamin C also recycles vitamin E in the membrane.

Everywhere else in the body

Each item, the places outside the cell where it is found or used, and what it does there.

Absorbing and clearing them

  • Small intestine. Absorbs most B vitamins and vitamin C through their own carriers.
  • Blood. Carries them to every tissue.
  • Kidneys. Send extra out in urine; riboflavin turns it bright yellow.

Thiamin (B1)

  • Brain and nerves. Need it to burn glucose; a shortage causes beriberi and, in heavy drinkers, Wernicke-Korsakoff syndrome.
  • Heart. A shortage can cause heart failure (wet beriberi).
  • Muscle. Holds about half the body’s thiamin.

Riboflavin (B2) and niacin (B3)

  • Mouth and skin. A riboflavin shortage cracks the corners of the mouth and makes the tongue sore.
  • Skin, gut and brain. A niacin shortage causes pellagra: rash on sun-exposed skin, diarrhea and confusion.
  • Liver. Makes some niacin from the amino acid tryptophan.
  • Skin blood vessels. High-dose niacin widens them: a hot flush.

Pantothenic acid (B5) and biotin (B7)

  • Every tissue. Pantothenic acid is part of coenzyme A, used to burn and build fats.
  • Liver. Biotin enzymes help make glucose and fatty acids.
  • Skin and hair. A biotin shortage causes rash and hair loss.
  • Large intestine. Bacteria make some biotin.

Vitamin B6

  • Brain. Needed to make serotonin, dopamine and GABA.
  • Bone marrow. Needed to make heme for new red blood cells.
  • Liver. Needed to process amino acids.
  • Muscle. Holds most of the body’s B6, in its glycogen enzyme.
  • Nerves. Very high supplement doses can damage them.

Folate

  • Bone marrow. Needed to make new red blood cells; a shortage causes large, immature red cells (megaloblastic anemia).
  • Embryo. Early in pregnancy it helps the neural tube close, preventing spina bifida.
  • Gut lining. Its fast-renewing cells need folate to copy DNA.
  • Liver. Stores some.
  • Blood. With B12 and B6 it keeps homocysteine low.

Vitamin B12

  • Stomach. Acid frees B12 from food, and the stomach lining makes intrinsic factor, which B12 needs to be absorbed.
  • Small intestine (ileum). Absorbs B12 bound to intrinsic factor at its far end.
  • Liver. Stores a few years’ supply.
  • Bone marrow. Needed to make red blood cells.
  • Nerves and spinal cord. Needed to keep myelin healthy; a shortage causes numbness and memory problems.
  • Large intestine. Bacteria make B12, but too far down to be absorbed.

Vitamin C

  • Skin, gums, blood vessels, tendons, bone and scars. Needed to make collagen; a shortage (scurvy) causes bleeding gums, bruising and poor wound healing.
  • Adrenal glands. Hold some of the highest levels; needed to make noradrenaline.
  • Brain. Also high; used to make noradrenaline.
  • Eyes. High in the lens and the fluid in front of it.
  • White blood cells. Concentrate it.
  • Small intestine. Helps absorb iron from plant foods.
  • Muscle. Needed to make carnitine, which carries fat into mitochondria.
  • Kidneys. Remove extra; very high doses can raise the risk of oxalate kidney stones.
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Figure 10

Putting It All Together

The whole lesson in one table, plus a few extras.

The nine water-soluble vitamins
VitaminMain jobToo littleWhole-food sources
B1 thiamincarbohydrate energy, nervesberiberipork, beans, whole grains, sunflower seeds
B2 riboflavincarries electronssore mouth and tonguemilk, eggs, almonds, mushrooms
B3 niacinNAD, hundreds of reactionspellagratuna, chicken, peanuts, mushrooms
B5 pantothenic acidcoenzyme Avery rarealmost every food
B6amino acids, neurotransmittersanemia, confusionchickpeas, fish, poultry, potatoes, bananas
B7 biotinadds CO2rare: hair, skineggs, salmon, seeds, sweet potato
B9 folateDNA, cell divisionanemia; neural tube defectslentils, leafy greens, asparagus
B12 cobalaminDNA, red cells, nervesanemia, nerve damageanimal foods only: clams, fish, meat, eggs, dairy
C ascorbic acidcollagen, iron, antioxidantscurvypeppers, kiwi, citrus, strawberries, broccoli
Worth knowing

Bright yellow urine

After a B-complex supplement, the extra riboflavin passes into urine and colors it bright yellow. It’s harmless.

Vitamin C and colds

Taking vitamin C regularly doesn’t prevent colds in most people; it may shorten them slightly.

Lime-treated corn

Corn’s niacin is tightly bound. Traditional cooking of corn with lime (nixtamalization, as for tortillas) frees it, which protected people from pellagra.

Choline

Choline is an essential nutrient grouped with the B vitamins, with an adequate intake of its own (550 mg men, 425 mg women); it is found in eggs, liver, meat, fish and soybeans.

General education, not medical advice. Facts follow mainstream sources (US Dietary Guidelines, NIH Office of Dietary Supplements, standard biochemistry and food-science texts).

Quiz

Tap a question to see the answer

1. Why do the B vitamins and vitamin C dissolve in water?

They have many oxygen and nitrogen atoms that form hydrogen bonds with water (Figure 1).

2. Which water-soluble vitamin is stored for years?

B12, in the liver (Figure 6).

3. What is a coenzyme?

A small non-protein helper an enzyme needs to work; B vitamins become coenzymes (Figure 2).

4. Do B vitamins provide energy?

No. They contain no usable calories; they help release energy from food (Figure 2).

5. Which deficiency disease comes from too little thiamin? From too little niacin?

Beriberi; pellagra (Figure 3).

6. Which two vitamins contain sulfur?

Thiamin (B1) and biotin (B7) (Figures 3 and 4).

7. Why is milk sold in opaque containers?

Light destroys riboflavin (Figure 3).

8. How does folic acid differ from the main food folate?

Folic acid lacks the four extra hydrogens and the methyl group; it is synthetic, stable and better absorbed (Figure 5).

9. Why is folic acid recommended for anyone who could become pregnant?

It lowers the risk of neural tube defects such as spina bifida (Figure 5).

10. What metal is at the center of vitamin B12?

Cobalt (Figure 6).

11. Why do vegans need fortified foods or a B12 supplement?

Only bacteria make B12 and plant foods don’t provide reliable amounts (Figure 6).

12. Name three things vitamin C does.

Keeps collagen-making enzymes working, helps absorb plant iron, acts as an antioxidant (Figure 7).

Next lesson: Module 2 · Major Minerals →