CID 5754

C₂₁H₃₀O₅

Cortisol

C 21
H 30
O 5

Ball-and-stick Stick Space-filling

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56 atoms, 59 bonds.

IUPAC name: (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Molar mass: 362.466(53) g/mol
Atoms: 56
SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O
InChIKey: JYGXADMDTFJGBT-VWUMJDOOSA-N
PubChem CID: 5754

Made of

C H O

Structural formula of cortisol. Each unlabelled corner is a carbon atom, and the 21 hydrogens on carbon are not drawn. Wedges come toward you, hashes go back. It shows which atoms are joined to which, not the shape. The model above shows the shape.

Two small glands sit on top of the kidneys, and the outer layer of each, the adrenal cortex, makes cortisol. The US National Cancer Institute (NCI) classes it as a glucocorticoid hormone. Glucocorticoids are steroid hormones involved in keeping up blood sugar and in the body’s response to stress, MedlinePlus Genetics says, and cholesterol has a part in making such hormones. MeSH, the subject vocabulary of the US National Library of Medicine, names cortisol the main glucocorticoid that the cortex secretes.

A molecule of C₂₁H₃₀O₅ holds 21 carbon, 30 hydrogen and five oxygen atoms, and a mole of it weighs 362.5 g. The pure substance is a white, crystalline powder, in the description of the Hazardous Substances Data Bank (HSDB), and melts with some decomposition at 217–220 °C.

Medicine knows the same molecule by a second name. Laboratory-made cortisol is called hydrocortisone, on the NCI’s definition, and is used as a medicine under that name.

Structure and bonding

Five oxygen atoms sit on cortisol’s frame of 21 carbons: three in O–H groups and two in C=O groups. The carbons form three six-membered rings and one five-membered ring, each sharing a C–C bond with the next; the Stick view shows that frame most plainly. One C=O belongs to the six-membered ring at one end, a single bond from the molecule’s only C=C. The other opens a two-carbon side chain on the five-membered ring.

Labels places the three O–H groups: on the side chain’s end carbon, on the hydrogen-free ring carbon carrying the chain, and on a CH in the neighbouring six-membered ring. ChEBI (Chemical Entities of Biological Interest) numbers these positions 21, 17 and 11, and the two C=O carbons 3 and 20.

In the Ball-and-stick view the four double-bonded carbons each hold three neighbours in one plane, the trigonal arrangement Chem1 describes. In the Space-filling view of PubChem’s computed model, the ring C=O oxygen and the side chain’s O–H oxygen lie 13.3 Å apart. The structural formula marks three bonds with solid wedges and one with a hashed wedge, for bonds rising above or dropping below its plane.

Where it turns up

Most of a person’s cortisol is in the blood, and some passes into urine and saliva, as MedlinePlus, the National Library of Medicine’s health site, describes. The level shifts through the day. It is normally highest in the morning, and the adrenals make less just after a person falls asleep, while stress and exercise can raise it. The LOTUS natural-products database also reports cortisol in Ganoderma boninense.

On a pharmacy shelf the molecule appears as hydrocortisone. A US Food and Drug Administration (FDA) monograph for over-the-counter products lets those made with hydrocortisone or hydrocortisone acetate carry the label “anti-itch”. The claim it permits is temporary relief of itching from minor skin irritation, inflammation and rashes.

The pure substance has come by two routes, HSDB notes: isolation from adrenal glands, and microbial transformation, a preparation patented in 1952. HSDB also gives it a veterinary use, as a glucocorticoid.

Why it matters

NICHD, one of the US National Institutes of Health, describes cortisol as a hormone the body cannot live without. It acts on nearly every organ and tissue, MedlinePlus says. It helps the body use glucose, protein and fats, on the NCI’s account, and NICHD credits it with maintaining blood pressure and heart function. ChEBI describes it as raising both blood sugar and blood pressure and reducing immune responses.

The amount made is set by a chain of signals that starts at the hypothalamus, a small region of the brain. It makes corticotropin-releasing hormone (CRH), which tells the pituitary gland to make adrenocorticotropic hormone (ACTH), and ACTH signals the adrenals to produce cortisol. Once cortisol has risen far enough it switches the CRH signal off, so both ACTH and cortisol drop.

The last step turns 11-deoxycortisol into cortisol with the help of the enzyme 11-beta-hydroxylase, and the release of ACTH triggers it. Progesterone is one of the earlier precursors. When another enzyme, 21-hydroxylase, is deficient, the substances normally used to form cortisol collect in the adrenals and become androgens instead.

Properties

Properties of cortisol Molar mass summed from IUPAC/CIAAW 2024 standard atomic weights; formula, atom and bond counts and PubChem's molecular weight from PubChem CID 5754.
Property	Value	Unit	Source
Molecular formula (Hill order)	C₂₁H₃₀O₅
Molar mass	362.466(53) g/mol	g/mol	IUPAC/CIAAW 2024
Carbon atoms	21
Hydrogen atoms	30
Oxygen atoms	5
Bonds	59
Single bonds	56
Double bonds	3
PubChem molecular weight	362.5 g/mol	g/mol	PubChem

Safety

Inside the body, a cortisol level that stays too high or too low is a serious matter when left untreated, MedlinePlus cautions. The pure substance carries the signal word Warning under the Globally Harmonized System (GHS). In 86.5% of the reports behind that classification it is suspected of damaging fertility or an unborn child; in 31.8% it may damage organs through prolonged or repeated exposure. Every statement is in the PubChem Laboratory Chemical Safety Summary for cortisol.

Questions

Why is cortisol called the stress hormone?

Cortisol helps the body respond to stress, the reason NIDDK, a US health institute, gives for the nickname. The ChEBI database ties the name to its part in the response to stress and anxiety. The adrenal glands make more cortisol under stress, and exercise raises it too. Protecting the body from stress is among the jobs MedlinePlus Genetics lists, beside keeping up blood sugar and suppressing inflammation.

What is hydrocortisone?

Hydrocortisone is cortisol under its medical name: the US National Cancer Institute defines it as cortisol made in a laboratory. It is used against inflammation and allergies, for certain hormone shortages and in treating some cancers. The institute's thesaurus describes it as acting on the glucocorticoid receptor to suppress immune and inflammatory responses. It is on the World Health Organization's Model List of Essential Medicines and was first approved as a drug in 1952.

How is cortisone related to cortisol?

Cortisone is cortisol with one group changed. Cortisol has an O–H on a ring carbon that the ChEBI database numbers 11. The index name for cortisone in MeSH, a US medical vocabulary, puts an oxo group, C=O, at that position instead. Cortisone has three C=O groups and two O–H groups; the cortisol model has two and three. Cortisone is inactive, and the liver converts it to hydrocortisone, the active form.

What happens when the body has too much or too little cortisol?

Too much cortisol over a long period is Cushing's syndrome, named for Harvey Cushing, a brain surgeon and the first to describe it. Long-term use of cortisol-like glucocorticoid medicines is its most common cause, according to NIDDK, a US health institute; tumours of the pituitary, the adrenals or elsewhere are the others. Too little cortisol comes from damaged adrenal glands, which is Addison's disease, or from a pituitary making too little of the hormone ACTH.

Made of the same elements

C₂₁H₃₀O₂ Progesterone 53 atoms, 56 bonds.
C₁₉H₂₈O₂ Testosterone 49 atoms, 52 bonds.
C₁₈H₃₄O₂ Oleic acid 54 atoms, 53 bonds.
C₁₆H₃₂O₂ Palmitic acid 50 atoms, 49 bonds.
C₁₈H₂₄O₂ Estradiol 44 atoms, 47 bonds.
C₂₀H₁₄O₄ Phenolphthalein 38 atoms, 41 bonds.
C₁₅H₁₆O₂ Bisphenol A 33 atoms, 34 bonds.
C₁₃H₁₈O₂ Ibuprofen 33 atoms, 33 bonds.

All 51 compounds made of carbon, hydrogen and oxygen

C₁₂H₂₂O₁₁ Lactose 45 atoms, 46 single bonds.
C₁₂H₂₂O₁₁ Sucrose 45 atoms, 46 single bonds.
C₂₇H₄₄O Cholecalciferol 72 atoms, 74 bonds.
C₁₀H₂₀O Menthol 31 atoms, 31 single bonds.
C₁₄H₁₄O₃ Naproxen 31 atoms, 32 bonds.
C₂₇H₄₆O Cholesterol 74 atoms, 77 bonds.
C₆H₁₂O₆ Fructose 24 atoms, 24 single bonds.
C₆H₁₂O₆ Glucose 24 atoms, 24 single bonds.
C₉H₈O₄ Aspirin 21 atoms, 21 bonds.
C₈H₈O₃ Methyl salicylate 19 atoms, 19 bonds.
C₈H₈O₃ Vanillin 19 atoms, 19 bonds.
C₆H₈O₆ Ascorbic acid 20 atoms, 20 bonds.
C₆H₈O₇ Citric acid 21 atoms, 20 bonds.
C₇H₆O₃ Salicylic acid 16 atoms, 16 bonds.
C₄H₉OH 1-Butanol 15 atoms, 14 single bonds.
C₆H₅COOH Benzoic acid 15 atoms, 15 bonds.
C₂H₅OC₂H₅ Diethyl ether 15 atoms, 14 single bonds.
C₄H₆O₅ Malic acid 15 atoms, 14 bonds.
C₆H₅CHO Benzaldehyde 14 atoms, 14 bonds.
C₃H₇COOH Butyric acid 14 atoms, 13 bonds.
CH₃COOC₂H₅ Ethyl acetate 14 atoms, 13 bonds.
C₃H₈O₃ Glycerol 14 atoms, 13 single bonds.
C₄H₆O₆ Tartaric acid 16 atoms, 15 bonds.
C₄H₈O Butanone 13 atoms, 12 bonds.
C₆H₅OH Phenol 13 atoms, 13 bonds.
C₃H₈O₂ Propylene glycol 13 atoms, 12 single bonds.
C₃H₇OH 1-Propanol 12 atoms, 11 single bonds.
C₃H₈O Isopropyl alcohol 12 atoms, 11 single bonds.
C₃H₆O₃ Lactic acid 12 atoms, 11 bonds.
C₂H₅COOH Propionic acid 11 atoms, 10 bonds.
C₃H₆O Acetone 10 atoms, 9 bonds.
C₂H₆O₂ Ethylene glycol 10 atoms, 9 single bonds.
CH₃OCH₃ Dimethyl ether 9 atoms, 8 single bonds.
C₂H₅OH Ethanol 9 atoms, 8 single bonds.
C₂H₄O₃ Glycolic acid 9 atoms, 8 bonds.
CH₃COOH Acetic acid 8 atoms, 7 bonds.
H₂C₂O₄ Oxalic acid 8 atoms, 7 bonds.
CH₃CHO Acetaldehyde 7 atoms, 6 bonds.
C₂H₄O Ethylene oxide 7 atoms, 7 single bonds.
H₂CO₃ Carbonic acid 6 atoms, 5 bonds.
CH₃OH Methanol 6 atoms, 5 single bonds.
HCOOH Formic acid 5 atoms, 4 bonds.
CH₂O Formaldehyde 4 atoms, 3 bonds.